| Date of match | Type of match | Name of team | Name of team | Score | Attendance |
| 30 August 1919 | Southern League | Southend United | Portsmouth | 0-2 | |
| 1 September 1919 | Southern League | Southend United | Newport County | 3-0 | |
| 13 September 1919 | Southern League | Southend United | Crystal Palace | 1-1 | |
| 4 October 1919 | Southern League | Southend United | Brentford | 2-1 | |
| 18 October 1919 | Southern League | Southend United | Plymouth Argyle | 1-0 | |
| 1 November 1919 | Southern League | Southend United | Reading | 2-2 | |
| 15 November 1919 | Southern League | Southend United | Luton Town | 3-0 | |
| 29 November 1919 | Southern League | Southend United | Swansea Town | 2-2 | |
| 13 December 1919 | Southern League | Southend United | Cardiff City | 1-1 | |
| 20 December 1919 | FA Cup 6th qualifying round | Southend United | Watford | 1-0 | |
| 25 December 1919 | Southern League | Southend United | Millwall | 1-0 | |
| 27 December 1919 | Southern League | Southend United | Swindon Town | 0-1 | |
| 17 January 1920 | Southern League | Southend United | Northampton Town | 0-0 | |
| 31 January 1920 | Southern League | Southend United | Watford | 4-1 | |
| 7 February 1920 | Southern League | Southend United | Norwich City | 1-1 | |
| 21 February 1920 | Southern League | Southend United | Merthyr Town | 2-1 | |
| 6 March 1920 | Southern League | Southend United | Bristol Rovers | 1-1 | |
| 20 March 1920 | Southern League | Southend United | Southampton | 2-1 | |
| 5 April 1920 | Southern League | Southend United | Brighton & Hove Albion | 0-0 | |
| 17 April 1920 | Southern League | Southend United | Exeter City | 2-0 | |
| 26 April 1920 | Southern League | Southend United | Queen's Park Rangers | 2-2 | |
| 28 August 1920 | Football League Division Three | Southend United | Brighton & Hove Albion | 0-0 | 9,000 |
| 6 September 1920 | Football League Division Three | Southend United | Grimsby Town | 3-1 | 7,000 |
| 11 September 1920 | Football League Division Three | Southend United | Swindon Town | 1-3 | 8,000 |
| 2 October 1920 | Football League Division Three | Southend United | Watford | 4-1 | 8,290 |
| 16 October 1920 | Football League Division Three | Southend United | Queen's Park Rangers | 1-0 | 8,000 |
| 23 October 1920 | Football League Division Three | Southend United | Northampton Town | 1-2 | 8,000 |
| 6 November 1920 | Football League Division Three | Southend United | Portsmouth | 2-1 | 8,000 |
| 27 November 1920 | Football League Division Three | Southend United | Merthyr Town | 0-1 | 8,000 |
| 4 December 1920 | Football League Diviion Three | Southend United | Plymouth Argyle | 2-1 | 4,000 |
| 18 December 1920 | FA Cup 6th qualifying round | Southend United | Hednesford Town | 3-1 | 4,445 |
| 27 December 1920 | Football League Division Three | Southend United | Newport County | 2-1 | 10,000 |
| 1 January 1921 | Football League Division Three | Southend United | Exeter City | 0-0 | 3,000 |
| 8 January 1921 | FA Cup 1st round | Southend United | Eccles United | 5-1 | 7,063 |
| 15 January 1921 | Football League Division Three | Southend United | Swansea Town | 1-2 | 6,000 |
| 29 January 1921 | FA Cup 2nd round | Southend United | Blackpool | 1-0 | 9,250 |
| 12 February 1921 | Football League Division Three | Southend United | Luton Town | 1-1 | 7,000 |
| 19 February 1921 | FA Cup 3rd round | Southend United | Tottenham Hotspur | 1-4 | 11,661 |
| 26 February 1921 | Football League Division Three | Southend United | Southampton | 1-0 | 11,000 |
| 12 March 1921 | Football League Division Three | Southend United | Reading | 1-0 | 7,000 |
| 28 March 1921 | Football League Division Three | Southend United | Gillingham | 1-0 | 10,000 |
| 2 April 1921 | Football League Division Three | Southend United | Bristol Rovers | 1-0 | 7,000 |
| 6 April 1921 | Football League Division Three | Southend United | Millwall | 1-2 | 6,000 |
| 16 April 1921 | Football League Division Three | Southend United | Brentford | 4-1 | 6,000 |
| 30 April 1921 | Football League Division Three | Southend United | Norwich City | 3-1 | 6,000 |
| 7 May 1921 | Football League Division Three | Southend United | Crystal Palace | 0-2 | 6,500 |
| 29 August 1921 | Football League Division Three (South) | Southend United | Brentford | 1-1 | 7,000 |
| 3 September 1921 | Football League Division Three (South) | Southend United | Brighton & Hove Albion | 1-2 | 7,000 |
| 17 September 1921 | Football League Division Three (South) | Southend United | Swansea Town | 1-0 | 6,000 |
| 1 October 1921 | Football League Division Three (South) | Southend United | Exeter City | 0-1 | 6,000 |
| 15 October 1921 | Football League Division Three (South) | Southend United | Millwall | 1-1 | 8,000 |
| 29 October 1921 | Football League Division Three (South) | Southend United | Gillingham | 2-0 | 6,000 |
| 12 November 1921 | Football League Division Three (South) | Southend United | Luton Town | 0-1 | 6,000 |
| 19 November 1921 | Football League Division Three (South) | Southend United | Aberdare Athletic | 3-2 | 7,000 |
| 10 December 1921 | Football League Division Three (South) | Southend United | Newport County | 0-1 | 7,000 |
| 24 December 1921 | Football League Division Three (South) | Southend United | Plymouth Argyle | 1-0 | 8,000 |
| 26 December 1921 | Football League Division Three (South) | Southend United | Portsmouth | 1-2 | 8,000 |
| 31 December 1921 | Football League Division Three (South) | Southend United | Merthyr Town | 2-1 | 6,000 |
| 28 January 1922 | FA Cup 2nd round | Southend United | Swansea Town | 0-2 | 10,400 |
| 11 February 1922 | Football League Division Three (South) | Southend United | Charlton Athletic | 1-1 | 8,000 |
| 25 February 1922 | Football League Division Three (South) | Southend United | Northampton Town | 1-1 | 8,000 |
| 11 March 1922 | Football League Division Three (South) | Southend United | Southampton | 0-0 | 7,000 |
| 18 March 1922 | Football League Division Three (South) | Southend United | Queen's Park Rangers | 1-2 | 7,000 |
| 1 April 1922 | Football League Division Three (South) | Southend United | Norwich City | 0-1 | 4,000 |
| 14 April 1922 | Football League Division Three (South) | Southend United | Swindon Town | 1-2 | 8,000 |
| 15 April 1922 | Football League Division Three (South) | Southend United | Reading | 2-0 | 5,000 |
| 26 April 1922 | Football League Division Three (South) | Southend United | Watford | 1-4 | 1,500 |
| 29 April 1922 | Football League Division Three (South) | Southend United | Bristol Rovers | 3-0 | 5,000 |
| 2 September 1922 | Football League Division Three (South) | Southend United | Newport County | 3-1 | 11,000 |
| 16 September 1922 | Football League Division Three (South) | Southend United | Swansea Town | 0-1 | 10,000 |
| 25 September 1922 | Football League Division Three (South) | Southend United | Aberdare Athletic | 4-0 | 8,000 |
| 30 September 1922 | Football League Division Three (South) | Southend United | Norwich City | 3-1 | 9,000 |
| 14 October 1922 | Football League Division Three (South) | Southend United | Bristol Rovers | 0-0 | 9,000 |
| 28 October 1922 | Football League Division Three (South) | Southend United | Bristol City | 0-3 | 6,000 |
| 4 November 1922 | Football League Division Three (South) | Southend United | Northampton Town | 1-2 | 7,000 |
| 22 November 1922 | FA Cup 4th qualifying round replay | Southend United | Sittingbourne | 4-2 | 5,000 |
| 2 December 1922 | FA Cup 5th qualifying round | Southend United | Norwich City | 2-2 | 8,514 |
| 16 December 1922 | Football League Division Three (South) | Southend United | Exeter City | 5-0 | 3,000 |
| 23 December 1922 | Football League Division Three (South) | Southend United | Charlton Athletic | 0-0 | 7,000 |
| 25 December 1922 | Football League Division Three (South) | Southend United | Reading | 3-1 | 8,900 |
| 6 January 1923 | Football League Division Three (South) | Southend United | Merthyr Town | 1-1 | 7,000 |
| 20 January 1923 | Football League Division Three (South) | Southend United | Watford | 2-1 | 5,000 |
| 10 February 1923 | Football League Division Three (South) | Southend United | Portsmouth | 0-0 | 6,000 |
| 24 February 1923 | Football League Division Three (South) | Southend United | Millwall | 4-0 | 9,000 |
| 10 March 1923 | Football League Division Three (South) | Southend United | Luton Town | 1-3 | 8,000 |
| 17 March 1923 | Football League Division Three (South) | Southend United | Queen's Park Rangers | 2-0 | 7,000 |
| 31 March 1923 | Football League Division Three (South) | Southend United | Gillingham | 1-1 | 9,000 |
| 2 April 1923 | Football League Division Three (South) | Southend United | Brentford | 1-2 | 9,000 |
| 9 April 1923 | Football League Division Three (South) | Southend United | Plymouth Argyle | 2-1 | |
| 14 April 1923 | Football League Division Three (South) | Southend United | Brighton & Hove Albion | 0-0 | 8,000 |
| 28 April 1923 | Football League Division Three (South) | Southend United | Swindon Town | 2-0 | 6,000 |
| 27 August 1923 | Football League Division Three (South) | Southend United | Charlton Athletic | 2-2 | 8,000 |
| 1 September 1923 | Football League Division Three (South) | Southend United | Merthyr Town | 3-1 | 8,000 |
| 15 September 1923 | Football League Division Three (South) | Southend United | Newport County | 2-0 | 8,000 |
| 19 September 1923 | Football League Division Three (South) | Southend United | Portsmouth | 0-1 | 6,000 |
| 29 September 1923 | Football League Division Three (South) | Southend United | Bristol Rovers | 1-0 | 8,000 |
| 6 October 1923 | Football League Division Three (South) | Southend United | Millwall | 0-0 | 8,000 |
| 20 October 1923 | Football League Division Three (South) | Southend United | Brentford | 3-1 | 8,000 |
| 3 November 1923 | Football League Division Three (South) | Southend United | Bournemouth & Boscombe Athletic | 1-1 | 7,000 |
| 17 November 1923 | FA Cup 4th qualifying round | Southend United | King's Lynn | 1-0 | 6,577 |
| 8 December 1923 | Football League Division Three (South) | Southend United | Reading | 2-1 | 5,000 |
| 22 December 1923 | Football League Division Three (South) | Southend United | Exeter City | 0-0 | 3,000 |
| 25 December 1923 | Football League Division Three (South) | Southend United | Aberdare Athletic | 1-1 | 7,500 |
| 5 January 1924 | Football League Division Three (South) | Southend United | Luton Town | 1-1 | 7,000 |
| 26 January 1924 | Football League Division Three (South) | Southend United | Norwich City | 3-1 | 6,000 |
| 9 February 1924 | Football League Division Three (South) | Southend United | Swindon Town | 0-2 | 4,000 |
| 8 March 1924 | Football League Division Three (South) | Southend United | Swansea Town | 0-0 | 7,000 |
| 15 March 1924 | Football League Division Three (South) | Southend United | Northampton Town | 5-1 | 7,000 |
| 19 March 1924 | Football League Division Three (South) | Southend United | Watford | 3-0 | 7,114 |
| 29 March 1924 | Football League Division Three (South) | Southend United | Gillingham | 3-2 | 4,000 |
| 12 April 1924 | Football League Division Three (South) | Southend United | Queen's Park Rangers | 4-2 | 5,000 |
| 21 April 1924 | Football League Division Three (South) | Southend United | Brighton & Hove Albion | 1-0 | 9,000 |
| 26 April 1924 | Football League Division Three (South) | Southend United | Plymouth Argyle | 0-2 | 6,000 |
| 30 August 1924 | Football League Division Three (South) | Southend United | Charlton Athletic | 0-3 | 10,000 |
| 10 September 1924 | Football League Division Three (South) | Southend United | Merthyr Town | 2-1 | 6,000 |
| 13 September 1924 | Football League Division Three (South) | Southend United | Watford | 0-4 | 8,000 |
| 17 September 1924 | Football League Division Three (South) | Southend United | Queen's Park Rangers | 1-0 | 8,000 |
| 4 October 1924 | Football League Division Three (South) | Southend United | Bristol Rovers | 2-1 | 8,000 |
| 18 October 1924 | Football League Division Three (South) | Southend United | Swansea Town | 1-0 | 8,000 |
| 25 October 1924 | Football League Division Three (South) | Southend United | Brighton & Hove Albion | 2-0 | 7,500 |
| 8 November 1924 | Football League Division Three (South) | Southend United | Bristol City | 2-0 | 9,000 |
| 15 November 1924 | FA Cup 4th qualifying round | Southend United | London Caledonians | 3-3 | 8,097 |
| 22 November 1924 | Football League Division Three (South) | Southend United | Aberdare Athletic | 2-1 | 5,000 |
| 6 December 1924 | Football League Division Three (South) | Southend United | Brentford | 6-1 | 4,000 |
| 20 December 1924 | Football League Division Three (South) | Southend United | Luton Town | 2-1 | 6,000 |
| 26 December 1924 | Football League Division Three (South) | Southend United | Gillingham | 4-0 | 9,000 |
| 3 January 1925 | Football League Division Three (South) | Southend United | Northampton Town | 0-1 | 6,000 |
| 24 January 1925 | Football League Division Three (South) | Southend United | Bournemouth & Boscombe Athletic | 3-0 | 5,000 |
| 31 January 1925 | Football League Division Three (South) | Southend United | Newport County | 0-1 | 9,000 |
| 14 February 1925 | Football League Division Three (South) | Southend United | Exeter City | 3-0 | 9,000 |
| 7 March 1925 | Football League Division Three (South) | Southend United | Plymouth Argyle | 0-3 | 9,000 |
| 21 March 1925 | Football League Division Three (South) | Southend United | Swindon Town | 0-0 | 11,000 |
| 4 April 1925 | Football League Division Three (South) | Southend United | Norwich City | 0-1 | 7,000 |
| 13 April 1925 | Football League Division Three (South) | Southend United | Reading | 3-0 | 6,000 |
| 18 April 1925 | Football League Division Three (South) | Southend United | Millwall | 1-0 | 7,000 |
| 2 September 1925 | Football League Division Three (South) | Southend United | Brentford | 3-1 | 8,224 |
| 5 September 1925 | Football League Division Three (South) | Southend United | Reading | 2-2 | 8,450 |
| 12 September 1925 | Football League Division Three (South) | Southend United | Norwich City | 0-1 | 8,764 |
| 16 September 1925 | Football League Division Three (South) | Southend United | Watford | 0-1 | 4,799 |
| 26 September 1925 | Football League Division Three (South) | Southend United | Northampton Town | 6-1 | 7,332 |
| 10 October 1925 | Football League Division Three (South) | Southend United | Brighton & Hove Albion | 4-0 | 8,276 |
| 24 October 1925 | Football League Division Three (South) | Southend United | Charlton Athletic | 1-2 | 8,804 |
| 7 November 1925 | Football League Division Three (South) | Southend United | Exeter Cty | 3-1 | 6,845 |
| 21 November 1925 | Football League Division Three (South) | Southend United | Luton Town | 2-0 | 6,706 |
| 28 November 1925 | FA Cup 1st round | Southend United | Dulwich Hamlet | 5-1 | 11,864 |
| 5 December 1925 | Football League Division Three (South) | Southend United | Bristol Rovers | 3-1 | 5,661 |
| 12 December 1925 | FA Cup 2nd round | Southend United | Gillingham | 1-0 | 9,784 |
| 19 December 1925 | Football League Division Three (South) | Southend United | Merthyr Town | 5-1 | 6,142 |
| 26 December 1925 | Football League Division Three (South) | Southend United | Bristol City | 1-2 | 13,438 |
| 2 January 1926 | Football League Division Three (South) | Southend United | Plymouth Argyle | 2-0 | 7,545 |
| 9 January 1926 | FA Cup 3rd round | Southend United | Southport | 5-2 | 10,847 |
| 30 January 1926 | FA Cup 4th round | Southend United | Derby County | 4-1 | 14,225 |
| 13 February 1926 | Football League Division Three (South) | Southend United | Aberdare Athletic | 0-1 | 8,030 |
| 20 February 1926 | FA Cup 5th round | Southend United | Nottingham Forest | 0-1 | 18,153 |
| 27 February 1926 | Football League Division Three (South) | Southend United | Bournemouth & Boscombe Athletic | 3-0 | 6,417 |
| 13 March 1926 | Football League Division Three (South) | Southend United | Swindon Town | 3-0 | 6,796 |
| 17 March 1926 | Football League Division Three (South) | Southend United | Millwall | 0-2 | 4,222 |
| 27 March 1926 | Football League Division Three (South) | Southend United | Newport County | 4-1 | 6,124 |
| 5 April 1926 | Football League Division Three (South) | Southend United | Crystal Palace | 5-1 | 10,908 |
| 10 April 1926 | Football League Division Three (South) | Southend United | Queen's Park Rangers | 2-1 | 6,398 |
| 24 April 1926 | Football League Division Three (South) | Southend United | Gillingham | 1-1 | 6,083 |
| 30 August 1926 | Football League Division Three (South) | Southend United | Millwall | 1-1 | 8,000 |
| 4 September 1926 | Football League Division Three (South) | Southend United | Exeter City | 1-2 | 9,029 |
| 15 September 1926 | Football League Division Three (South) | Southend United | Brentford | 3-1 | 6,512 |
| 18 September 1926 | Football League Division Three (South) | Southend United | Aberdare Athletic | 5-1 | 8,058 |
| 25 September 1926 | Football League Division Three (South) | Southend United | Luton Town | 2-1 | 9,211 |
| 9 October 1926 | Football League Division Three (South) | Southend United | Brighton & Hove Albion | 0-1 | 7,369 |
| 23 October 1926 | Football League Division Three (South) | Southend United | Newport County | 5-0 | 6,481 |
| 6 November 1926 | Football League Division Three (South) | Southend United | Watford | 2-0 | 7,109 |
| 20 November 1926 | Football League Division Three (South) | Southend United | Coventry City | 3-1 | 3,681 |
| 4 December 1926 | Football League Division Three (South) | Southend United | Charlton Athletic | 5-0 | 7,255 |
| 18 December 1926 | Football League Division Three (South) | Southend United | Bournemouth & Boscombe Athletic | 0-3 | 6,058 |
| 27 December 1926 | Football League Division Three (South) | Southend United | Bristol Rovers | 2-1 | 11,091 |
| 15 January 1927 | Football League Division Three (South) | Southend United | Swindon Town | 2-2 | 7,118 |
| 29 January 1927 | Football League Division Three (South) | Southend United | Merthyr Town | 3-1 | 4,763 |
| 19 February 1927 | Football League Division Three (South) | Southend United | Norwich City | 3-3 | 6,517 |
| 5 March 1927 | Football League Division Three (South) | Southend United | Plymouth Argyle | 1-2 | 5,936 |
| 19 March 1927 | Football League Division Three (South) | Southend United | Gillingham | 1-0 | 6,605 |
| 2 April 1927 | Football League Division Three (South) | Southend United | Crystal Palace | 3-1 | 6,270 |
| 16 April 1927 | Football League Division Three (South) | Southend United | Queen's Park Rangers | 0-3 | 7,813 |
| 18 April 1927 | Football League Division Three (South) | Southend United | Northampton Town | 2-0 | 7,809 |
| 30 April 1927 | Football League Division Three (South) | Southend United | Bristol City | 0-1 | 6,608 |
| 27 August 1927 | Football League Division Three (South) | Southend United | Luton Town | 1-0 | 11,186 |
| 7 September 1927 | Football League Division Three (South) | Southend United | Bournemouth & Boscombe Athletic | 3-0 | 5,631 |
| 10 September 1927 | Football League Division Three (South) | Southend United | Crystal Palace | 6-1 | 6,808 |
| 24 September 1927 | Football League Division Three (South) | Southend United | Torquay United | 1-0 | 8,546 |
| 8 October 1927 | Football League Division Three (South) | Southend United | Northampton Town | 2-0 | 8,768 |
| 22 October 1927 | Football League Division Three (South) | Southend United | Merthyr Town | 2-1 | 3,774 |
| 5 November 1927 | Football League Division Three (South) | Southend United | Gillingham | 1-2 | 6,756 |
| 19 November 1927 | Football League Division Three (South) | Southend United | Bristol Rovers | 2-1 | 4,421 |
| 26 November 1927 | FA Cup 1st round | Southend United | Wellington Town | 1-0 | 5,000 |
| 3 December 1927 | Football League Division Three (South) | Southend United | Watford | 3-0 | 5,320 |
| 26 December 1927 | Football League Division Three (South) | Southend United | Brentford | 3-2 | 3,540 |
| 7 January 1928 | Football League Division Three (South) | Southend United | Millwall | 0-1 | 9,767 |
| 11 February 1928 | Football League Division Three (South) | Southend United | Norwich City | 1-1 | 4,671 |
| 15 February 1928 | Football League Division Three (South) | Southend United | Exeter City | 1-2 | 2,603 |
| 25 February 1928 | Football League Division Three (South) | Southend United | Coventry City | 3-2 | 5,979 |
| 10 March 1928 | Football League Division Three (South) | Southend United | Walsall | 2-1 | 4,736 |
| 14 March 1928 | Football League Division Three (South) | Southend United | Swindon Town | 1-1 | 3,159 |
| 24 March 1928 | Football League Division Three (South) | Southend United | Plymouth Argyle | 3-0 | 5,187 |
| 7 April 1928 | Football League Division Three (South) | Southend United | Queen's Park Rangers | 7-0 | 8,126 |
| 9 April 1928 | Football League Division Three (South) | Southend United | Brighton & Hove Albion | 0-1 | 10,407 |
| 21 April 1928 | Football League Division Three (South) | Southend United | Charlton Athletic | 1-2 | 4,501 |
| 5 May 1928 | Football League Division Three (South) | Southend United | Newport County | 5-1 | 4,796 |
| 27 August 1928 | Football League Division Three (South) | Southend United | Exeter City | 1-0 | 6,355 |
| 1 September 1928 | Football League Division Three (South) | Southend United | Brentford | 1-1 | 8,082 |
| 15 September 1928 | Football League Division Three (South) | Southend United | Coventry City | 0-0 | 7,243 |
| 29 September 1928 | Football League Division Three (South) | Southend United | Charlton Athletic | 1-3 | 8,144 |
| 13 October 1928 | Football League Division Three (South) | Southend United | Brighton & Hove Albion | 1-1 | 7,746 |
| 27 October 1928 | Football League Division Three (South) | Southend United | Fulham | 0-1 | 8,843 |
| 10 November 1928 | Football League Division Three (South) | Southend United | Bristol Rovers | 1-0 | 5,764 |
| 22 December 1928 | Football League Division Three (South) | Southend United | Torquay United | 3-0 | 4,096 |
| 26 December 1928 | Football League Division Three (South) | Southend United | Merthyr Town | 5-1 | 3,579 |
| 29 December 1928 | Football League Division Three (South) | Southend United | Bournemouth & Boscombe Athletic | 4-4 | 5,432 |
| 19 January 1929 | Football League Division Three (South) | Southend United | Luton Town | 5-0 | 6,153 |
| 2 February 1929 | Football League Division Three (South) | Southend United | Northampton Town | 2-2 | 5,944 |
| 16 February 1929 | Football League Division Three (South) | Southend United | Norwich City | 5-3 | 3,459 |
| 20 February 1929 | Football League Division Three (South) | Southend United | Walsall | 3-1 | 2,905 |
| 2 March 1929 | Football League Division Three (South) | Southend United | Plymouth Argyle | 1-1 | 6,486 |
| 16 March 1929 | Football League Division Three (South) | Southend United | Queen's Park Rangers | 0-3 | 6,259 |
| 30 March 1929 | Football League Division Three (South) | Southend United | Watford | 1-3 | 7,688 |
| 1 April 1929 | Football League Division Three (South) | Southend United | Gillingham | 2-0 | 7,773 |
| 10 April 1929 | Football League Division Three (South) | Southend United | Crystal Palace | 3-0 | 3,084 |
| 13 April 1929 | Football League Division Three (South) | Southend United | Newport County | 4-2 | 4,820 |
| 27 April 1929 | Football League Division Three (South) | Southend United | Swindon Town | 1-1 | 5,312 |
| 31 August 1929 | Football League Division Three (South) | Southend United | Newport County | 2-1 | 8,186 |
| 2 September 1929 | Football League Division Three (South) | Southend United | Crystal Palace | 3-2 | 6,954 |
| 14 September 1929 | Football League Division Three (South) | Southend United | Bournemouth & Boscombe Athletic | 4-1 | 9,577 |
| 16 September 1929 | Football League Division Three (South) | Southend United | Northampton Town | 1-2 | 8,145 |
| 28 September 1929 | Football League Division Three (South) | Southend United | Queen's Park Rangers | 1-0 | 10,867 |
| 12 October 1929 | Football League Division Three (South) | Southend United | Norwich City | 1-1 | 8,981 |
| 19 October 1929 | Football League Division Three (South) | Southend United | Torquay United | 1-1 | 8,269 |
| 2 November 1929 | Football League Division Three (South) | Southend United | Plymouth Argyle | 1-1 | 10,966 |
| 16 November 1929 | Football League Division Three (South) | Southend United | Brighton & Hove Albion | 0-0 | 3,553 |
| 30 November 1929 | FA Cup 1st round | Southend United | Brentford | 1-0 | 16,890 |
| 14 December 1929 | FA Cup 2nd round | Southend United | York City | 1-4 | 10,000 |
| 25 December 1929 | Football League Division Three (South) | Southend United | Exeter City | 1-0 | 6,154 |
| 4 January 1930 | Football League Division Three (South) | Southend United | Luton Town | 1-1 | 5,859 |
| 11 January 1930 | Football League Division Three (South) | Southend United | Brentford | 2-0 | 6,456 |
| 8 February 1930 | Football League Division Three (South) | Southend United | Fulham | 1-2 | 6,204 |
| 19 February 1930 | Football League Division Three (South) | Southend United | Walsall | 1-0 | 3,006 |
| 1 March 1930 | Football League Division Three (South) | Southend United | Merthyr Town | 6-0 | 5,583 |
| 15 March 1930 | Football League Division Three (South) | Southend United | Swindon Town | 3-1 | 6,106 |
| 29 March 1930 | Football League Division Three (South) | Southend United | Bristol Rovers | 6-0 | 5,903 |
| 12 April 1930 | Football League Division Three (South) | Southend United | Clapton Orient | 4-1 | 6,282 |
| 26 April 1930 | Football League Division Three (South) | Southend United | Watford | 1-3 | 4,495 |
| 30 April 1930 | Football League Division Three (South) | Southend United | Coventry City | 1-2 | 2,667 |
| 30 August 1930 | Football League Division Three (South) | Southend United | Crystal Palace | 2-4 | 7,413 |
| 8 September 1930 | Football League Division Three (South) | Southend United | Torquay United | 6-3 | 5,656 |
| 20 September 1930 | Football League Division Three (South) | Southend United | Bristol Rovers | 4-0 | 6,442 |
| 4 October 1930 | Football League Division Three (South) | Southend United | Gillingham | 3-2 | 7,476 |
| 18 October 1930 | Football League Division Three (South) | Southend United | Swindon Town | 5-3 | 7,532 |
| 1 November 1930 | Football League Division Three (South) | Southend United | Coventry City | 2-0 | 4,019 |
| 15 November 1930 | Football League Division Three (South) | Southend United | Queen's Park Rangers | 2-0 | 5,060 |
| 29 November 1930 | FA Cup 1st round | Southend United | Torquay United | 0-1 | 10,000 |
| 13 December 1930 | Football League Division Three (South) | Southend United | Bournemouth & Boscombe Athletic | 4-0 | 4,635 |
| 17 December 1930 | Football League Division Three (South) | Southend United | Notts County | 2-1 | 4,827 |
| 25 December 1930 | Football League Division Three (South) | Southend United | Northampton Town | 2-1 | 10,068 |
| 10 January 1931 | Football League Division Three (South) | Southend United | Thames | 1-0 | 1,830 |
| 17 January 1931 | Football League Division Three (South) | Southend United | Luton Town | 0-2 | 4,857 |
| 31 January 1931 | Football League Division Three (South) | Southend United | Newport County | 6-2 | 5,536 |
| 28 February 1931 | Football League Division Three (South) | Southend United | Fulham | 2-4 | 5,353 |
| 14 March 1931 | Football League Division Three (South) | Southend United | Walsall | 2-0 | 6,460 |
| 18 March 1931 | Football League Division Three (South) | Southend United | Exeter City | 5-1 | 4,097 |
| 28 March 1931 | Football League Division Three (South) | Southend United | Norwich City | 2-0 | 5,638 |
| 6 April 1931 | Football League Division Three (South) | Southend United | Brentford | 0-1 | 9,969 |
| 11 April 1931 | Football League Division Three (South) | Southend United | Clapton Orient | 2-0 | 5,791 |
| 25 April 1931 | Football League Division Three (South) | Southend United | Watford | 1-0 | 3,459 |
| 2 May 1931 | Football League Division Three (South) | Southend United | Brighton & Hove Albion | 0-2 | 5,758 |
| 29 August 1931 | Football League Division Three (South) | Southend United | Gillingham | 2-0 | 10,665 |
| 7 September 1931 | Football League Division Three (South) | Southend United | Thames | 1-1 | 7,461 |
| 12 September 1931 | Football League Division Three (South) | Southend United | Cardiff City | 1-1 | 7,494 |
| 26 September 1931 | Football League Division Three (South) | Southend United | Reading | 1-1 | 9,633 |
| 17 October 1931 | Football League Division Three (South) | Southend United | Swindon Town | 3-0 | 10,430 |
| 31 October 1931 | Football League Division Three (South) | Southend United | Brighton & Hove Albion | 2-0 | 10,488 |
| 14 November 1931 | Football League Division Three (South) | Southend United | Watford | 3-0 | 10,692 |
| 25 December 1931 | Football League Division Three (South) | Southend United | Exeter City | 0-1 | 9,845 |
| 9 January 1932 | Football League Division Three (South) | Southend United | Bristol Rovers | 4-1 | 6,220 |
| 13 January 1932 | Football League Division Three (South) | Southend United | Bournemouth & Boscombe Athletic | 1-3 | 4,227 |
| 16 January 1932 | Football League Division Three (South) | Southend United | Luton Town | 1-1 | 5,508 |
| 30 January 1932 | Football League Division Three (South) | Southend United | Northampton Town | 0-1 | 6,465 |
| 13 February 1932 | Football League Division Three (South) | Southend United | Clapton Orient | 1-3 | 4,714 |
| 20 February 1932 | Football League Division Three (South) | Southend United | Fulham | 4-1 | 6,330 |
| 5 March 1932 | Football League Division Three (South) | Southend United | Norwich City | 2-0 | 7,262 |
| 19 March 1932 | Football League Division Three (South) | Southend United | Mansfield Town | 5-2 | 6,710 |
| 28 March 1932 | Football League Division Three (South) | Southend United | Brentford | 1-0 | 17,313 |
| 2 April 1932 | Football League Division Three (South) | Southend United | Crystal Palace | 1-0 | 8,745 |
| 16 April 1932 | Football League Division Three (South) | Southend United | Queen's Park Rangers | 0-0 | 5,669 |
| 30 April 1932 | Football League Division Three (South) | Southend United | Torquay United | 4-2 | 5,471 |
| 7 May 1932 | Football League Division Three (South) | Southend United | Coventry City | 4-0 | 6,356 |
| 29 August 1932 | Football League Division Three (South) | Southend United | Bristol Rovers | 2-2 | 8,677 |
| 3 September 1932 | Football League Division Three (South) | Southend United | Queen's Park Rangers | 0-1 | 7,408 |
| 14 September 1932 | Football League Division Three (South) | Southend United | Newport County | 3-0 | 5,687 |
| 24 September 1932 | Football League Division Three (South) | Southend United | Gillingham | 2-2 | 5,278 |
| 8 October 1932 | Football League Division Three (South) | Southend United | Cardiff City | 2-2 | 3,590 |
| 22 October 1932 | Football League Division Three (South) | Southend United | Brentford | 0-1 | 9,453 |
| 5 November 1932 | Football League Division Three (South) | Southend United | Bristol City | 3-1 | 7,017 |
| 19 November 1932 | Football League Division Three (South) | Southend United | Clapton Orient | 3-3 | 4,901 |
| 26 November 1932 | FA Cup 1st round | Southend United | Exeter City | 1-1 | 8,565 |
| 3 December 1932 | Football League Division Three (South) | Southend United | Bournemouth & Boscombe Athletic | 2-1 | 6,014 |
| 10 December 1932 | FA Cup 2nd round | Southend United | Scarborough | 4-1 | 8,000 |
| 17 December 1932 | Football League Division Three (South) | Southend United | Luton Town | 2-1 | 6,057 |
| 26 December 1932 | Football League Division Three (South) | Southend United | Norwich City | 2-1 | 8,342 |
| 31 December 1932 | Football League Division Three (South) | Southend United | Aldershot | 5-1 | 6,087 |
| 18 January 1933 | FA Cup 3rd round replay | Southend United | Watford | 2-0 | 8,036 |
| 21 January 1933 | Football League Division Three (South) | Southend United | Torquay United | 2-1 | 5,570 |
| 28 January 1933 | FA Cup 4th round | Southend United | Derby County | 2-3 | 15,188 |
| 1 February 1933 | Football League Division Three (South) | Southend United | Crystal Palace | 1-2 | 3,008 |
| 11 February 1933 | Football League Division Three (South) | Southend United | Watford | 2-1 | 5,048 |
| 25 February 1933 | Football League Division Three (South) | Southend United | Reading | 3-1 | 4,384 |
| 11 March 1933 | Football League Division Three (South) | Southend United | Coventry City | 1-3 | 5,958 |
| 25 March 1933 | Football League Division Three (South) | Southend United | Northampton Town | 1-0 | 5,670 |
| 8 April 1933 | Football League Division Three (South) | Southend United | Swindon Town | 0-0 | 5,383 |
| 17 April 1933 | Football League Division Three (South) | Southend United | Brighton & Hove Albion | 2-1 | 8,372 |
| 6 May 1933 | Football League Division Three (South) | Southend United | Exeter City | 1-2 | 5,848 |
| 26 August 1933 | Football League Division Three (South) | Southend United | Crystal Palace | 0-4 | 10,285 |
| 6 September 1933 | Football League Division Three (South) | Southend United | Gillingham | 1-2 | 7,208 |
| 9 September 1933 | Football League Division Three (South) | Southend United | Clapton Orient | 2-1 | 8,927 |
| 16 September 1933 | Football League Division Three (South) | Southend United | Coventry City | 2-1 | 7,666 |
| 30 September 1933 | Football League Division Three (South) | Southend United | Watford | 1-1 | 6,799 |
| 14 October 1933 | Football League Division Three (South) | Southend United | Bournemouth & Boscombe Athletic | 1-2 | 4,809 |
| 28 October 1933 | Football League Division Three (South) | Southend United | Brighton & Hove Albion | 0-0 | 5,803 |
| 11 November 1933 | Football League Division Three (South) | Southend United | Luton Town | 0-1 | 5,828 |
| 9 December 1933 | FA Cup 2nd round | Southend United | Chester | 2-1 | 6,524 |
| 23 December 1933 | Football League Division Three (South) | Southend United | Bristol City | 3-0 | 4,549 |
| 26 December 1933 | Football League Division Three (South) | Southend United | Exeter City | 3-1 | 4,828 |
| 6 January 1934 | Football League Division Three (South) | Southend United | Bristol Rovers | 2-2 | 5,960 |
| 17 January 1934 | Football League Division Three (South) | Southend United | Torquay United | 3-1 | 2,732 |
| 3 February 1934 | Football League Division Three (South) | Southend United | Reading | 2-2 | 3,054 |
| 17 February 1934 | Football League Division Three (South) | Southend United | Charlton Athletic | 1-0 | 5,655 |
| 3 March 1934 | Football League Division Three (South) | Southend United | Swindon Town | 4-1 | 5,869 |
| 14 March 1934 | Football League Division Three (South) | Southend United | Newport County | 3-5 | 2,580 |
| 17 March 1934 | Football League Division Three (South) | Southend United | Aldershot | 1-0 | 4,865 |
| 31 March 1934 | Football League Division Three (South) | Southend United | Northampton Town | 2-0 | 6,513 |
| 2 April 1934 | Football League Division Three (South) | Southend United | Cardiff City | 1-1 | 9,303 |
| 14 April 1934 | Football League Division Three (South) | Southend United | Queen's Park Rangers | 0-2 | 5,249 |
| 28 April 1934 | Football League Division Three (South) | Southend United | Norwich City | 0-0 | 4,700 |
