Southern Professional Floodlit Cup 1959-60 
Winners: Coventry City Runners-up: West Ham United Winners from previous season: Arsenal First round
| | 13 October 1959 | West Ham United | 3 | - | 1 | Millwall | 8,200 | Boleyn Ground, London | | | Doug Wragg (2), Malcolm Musgrove
| | | | Alec Moyse | | | | 26 October 1959 | Queen's Park Rangers | 1 | - | 2 | Leyton Orient | 5,758 | Loftus Road, London | | | Arthur Longbottom
| | | | Bobby Brown, Ken Facey (pen.)
| | | | Second round | | 19 October 1959 | Southend United | 0 | - | 0 | Coventry City | 6,692 | Roots Hall, Southend | | 21 October 1959 | Crystal Palace | 5 | - | 2 | Brentford | 6,600 | Selhurst Park, London | | | Harry Easton (4), Dave Sexton
| | | | George Francis (2)
| | | | 21 October 1959 | Leicester City | 4 | - | 0 | Charlton Athletic | 7,129 | Filbert Street, Leicester | | | Howard Riley, Colin Appleton, Frank McLintock, Albert Cheesebrough
| | | | | | | | 26 October 1959 | Luton Town | 1 | - | 1 | Fulham | 5,008 | Kenilworth Road, Luton | | | John Warner
| | | | Trevor 'Tosh' Chamberlain
| | | | 26 October 1959 | Southampton | 3 | - | 0 | Aldershot | 3,979 | The Dell, Southampton | | | Terry Paine (2), George O'Brien
| | | | | | | | 26 October 1959 | West Ham United | 6 | - | 1 | Reading | 5,400 | Boleyn Ground, London | | | Mike Grice, Harry Obeney (4), Andy Smillie
| | | | Bernard Goodall
| | | | 27 October 1959 | Arsenal | 2 | - | 1 | Portsmouth | 4,108 | Highbury, London | | | Jimmy Bloomfield, Len Julians
| | | | Reg Cutler
| | | | 3 November 1959 | Watford | 0 | - | 2 | Leyton Orient | 4,064 | Vicarage Road, Watford | | | | | | | Tommy Johnston, Eddie Brown | | | Replays
| | 26 October 1959 | Coventry City | 4 | - | 0 | Southend United | 6,813 | Highfield Road, Coventry | | | Alan 'Digger' Daley, Ken Simcoe (2), Ken Satchwell
| | | | | | | | 23 November 1959 | Fulham | 1 | - | 0 | Luton Town | 10,100 | Griffin Park, London | | | Trevor 'Tosh' Chamberlain | | | | | | | Quarter-Finals
| | 23 November 1959 | Arsenal | 4 | - | 2 | Leicester City | 6,402 | Highbury, London | | | Jackie Henderson, Jimmy Bloomfield, Joe Haverty, Graham Willis
| | | | Gordon Wills, Jimmy Walsh
| | | | 7 December 1959 | West Ham United | 4 | - | 3 | Leyton Orient | 8,606 | Boleyn Ground, London | | | John Bond, Phil Woosnam, Malcolm Musgrove (2)
| | | | Eddy Brown, Terry McDonald, Phil White
| | | | 14 December 1959 | Crystal Palace | 2 | - | 2 | Southampton | 6,136 | Selhurst Park, London | | | Johnny Byrne, Tommy Barnett
| | | | Derek Reeves, George O'Brien
| | | | 18 January 1960 | Coventry City | 1 | - | 1 | Fulham | 15,309 | Highfield Road, Coventry | | | Ken Satchwell
| | | | Jimmy Langley
| | | | Replays | | 18 January 1960 | Southampton | 2 | - | 1 | Crystal Palace | 6,151 | The Dell, Southampton | | | Derek Reeves (2)
| | | | Johnny Roche
| | | | 1 February 1960 | Fulham | 0 | - | 1 | Coventry City | 4,800 | Griffin Park, London | | | | | | | Colin Hawkins
| | | Semi-finals
| | 28 March 1960 | Coventry City | 2 | - | 1 | Southampton | 11,773 | Highfield Road, Coventry | | | Ray Straw (2)
| | | | Brown
| | | | 5 April 1960 | Arsenal | 1 | - | 3 | West Ham United | 8,000 | Highbury, London | | | Tommy Docherty
| | | | Johnny Cartwright (2), Malcolm Musgrove
| | | Final | | 27 April 1960 | Coventry City | 2 | - | 1 | West Ham United | 16,921 | Highfield Road, Coventry | | | Ron Hewitt (2)
| | | | Johnny Cartwright
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