Division Three (South) Cup 1937-38 
Winners: Reading Runners-up: Bristol City Winners from previous season: Millwall & Watford (trophy shared) First round
| | 29 September 1937 | Aldershot | 1 | - | 1 | Walsall | 1,500 | Recreation Ground, Aldershot | | | Harry Egan
| | | | Doug Redwood
| | | | 6 October 1937 | Bournemouth & Boscombe Athletic | 1 | - | 2 | Reading | 2,000 | Dean Court, Bournemouth | | | Joe Riley
| | | | Bill Layton, Gilbert Glidden
| | | | 6 October 1937 | Bristol City | 3 | - | 0 | Torquay United | 1,337 | Ashton Gate, Bristol | | | Jack Dryden (2, 1 pen.), Jack Haycox
| | | | | | | | 27 September 1937 | Cardiff City | 1 | - | 0 | Northampton Town | 3,869 | Ninian Park, Cardiff | | | Bert Turner
| | | | | | | | 29 September 1937 | Gillingham | 3 | - | 1 | Brighton & Hove Albion | 2,000 | Priestfield Stadium, Gillingham | | | Tom Wilson (2), Cyril Walker | | | | Stan Risdon
| | | | 27 September 1937 | Mansfield Town | 0 | - | 1 | Crystal Palace | 1,500 | Field Mill, Mansfield | | | | | | | Bert Robson
| | | | 21 October 1937 | Newport County | 2 | - | 2 | Watford | 1,000 | Somerton Park, Newport | | | Tommy Wood (2) | | | | Tom Walters (2)
| | | | 22 September 1937 | Southend United | 1 | - | 2 | Exeter City | 2,580 | Southend Stadium, Southend | | | Sam Bell
| | | | Harry Bowl (2)
| | | | Bye | Bristol Rovers | | | | | | | | Bye | Clapton Orient | | | | | | | | Bye | Millwall | | | | | | | | Bye | Notts County | | | | | | | | Bye | Queen's Park Rangers | | | | | | | | Bye | Swindon Town | | | | | | | Replays | | 18 October 1937 | Walsall | 2 | - | 1 | Aldershot | 200 | Fellows Park, Walsall | | | Charlie Bulger, Bill Evans
| | | | Harry Butt
| | | | 27 October 1937 | Watford | 4 | - | 0 | Newport County | 261 | Vicarage Road, Watford | | | George Lewis (2), Joe Brown, Tom Moran (pen.)
| | | | | | | Second round
| | 10 November 1937 | Bristol City | 2 | - | 1 | Cardiff City | 2,130 | Ashton Gate, Bristol | | | Joe Brain, Jack Haycox
| | | | Jimmy Collins
| | | | 17 November 1937 | Bristol Rovers | 5 | - | 0 | Crystal Palace | | Eastville, Bristol | | | Bill Pendergasdt (2), Bert Iles (2), Tom Harris | | | | | | | | 8 November 1937 | Millwall | 4 | - | 0 | Gillingham | 2,000 | The Den, London | | | Dave Mangnall (3), Reg Smith
| | | | | | | | 10 November 1937 | Notts County | 0 | - | 2 | Watford | 1,000 | Meadow Lane, Nottingham | | | | | | | George Lewis, Ralph Evans
| | | | 11 November 1937 | Queen's Park Rangers | 2 | - | 0 | Clapton Orient | 3,500 | Loftus Road, London | | | Alf Fitzgerald, Harry Lowe | | | | | | | | 17 November 1937 | Swindon Town | 2 | - | 0 | Exeter City | 900 | County Ground, Swindon | | | Bill Lucas, Don Emery (pen.)
| | | | | | | | Bye | Reading | | | | | | | | Bye | Walsall | | | | | | | Quarter-finals
| | 28 February 1938 | Queen's Park Rangers | 2 | - | 3 | Watford | 2,095 | Loftus Road, London | | | Len McCarthy
| | | | Tom Walters (2), David Laing
| | | | 2 February 1938 | Reading | 3 | - | 1 | Bristol Rovers | 1,392 | Elm Park, Reading | | | Tommy Tait, Peter Simpson, Willie Cook
| | | | Bobby Gardiner
| | | | 16 February 1938 | Swindon Town | 1 | - | 2 | Millwall | 922 | County Ground, Swindon | | | Geoffrey Moreland
| | | | John McLeod, Bob Thomas
| | | | 10 January 1938 | Walsall | 1 | - | 2 | Bristol City | 526 | Fellows Park, Walsall | | | Doug Redwood
| | | | Joe Brain, Duncan Colquhoun
| | | Semi-finals
| | 30 March 1938 | Bristol City | 2 | - | 0 | Millwall | 1,513 | Ashton Gate, Bristol | | | Joe Brain, Lew Booth | | | | | | | | 16 March 1938 | Reading | 3 | - | 0 | Watford | 1,629 | Elm Park, Reading | | | Tommy Tait (2), Peter Simpson
| | | | | | | Final
| 1st leg | | 28 September 1938 | Reading | 6 | - | 1 | Bristol City | 1,097 | Elm Park, Reading | | | Tony MacPhee (4), Fred Smallwood, Tommy Tait | | | | George Willshaw
| | | | 2nd leg | | 12 October 1938 | Bristol City | 1 | - | 0 | Reading | 718 | Ashton Gate, Bristol | | | Joe Brain
| | | | | | | | | (Reading win 6-2 on aggregate) | | |
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