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 | | 6 October 1937 | Bournemouth & Boscombe Athletic | 1 | - | 2 | Reading | 2,000 | Dean Court, Bournemouth | | 6 October 1937 | Bristol City | 3 | - | 0 | Torquay United | 1,337 | Ashton Gate, Bristol | | 27 September 1937 | Cardiff City | 1 | - | 0 | Northampton Town | 3,869 | Ninian Park, Cardiff | | 28 September 1937 | Gillingham | 3 | - | 1 | Brighton & Hove Albion | 2,000 | Priestfield Stadium, Gillingham | | 27 September 1937 | Mansfield Town | 0 | - | 1 | Crystal Palace | 1,500 | Field Mill, Mansfield | | 21 October 1937 | Newport County | 2 | - | 2 | Watford | 1,000 | Somerton Park, Newport | | 22 September 1937 | Southend United | 1 | - | 2 | Exeter City | 2,580 | Southend Stadium, Southend | | 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 | | 27 October 1937 | Watford | 4 | - | 0 | Newport County | 261 | Vicarage Road, Watford | Second round
| | 10 November 1937 | Bristol City | 2 | - | 1 | Cardiff City | 2,130 | Ashton Gate, Bristol | | 17 November 1937 | Bristol Rovers | 5 | - | 0 | Crystal Palace | | Eastville, Bristol | | 8 November 1937 | Millwall | 4 | - | 0 | Gillingham | 2,000 | The Den, London | | 10 November 1937 | Notts County | 0 | - | 2 | Watford | 1,000 | Meadow Lane, Nottingham | | 11 November 1937 | Queen's Park Rangers | 2 | - | 0 | Clapton Orient | 3,500 | Loftus Road, London | | 17 November 1937 | Swindon Town | 2 | - | 0 | Exeter City | 900 | County Ground, Swindon | | Bye | Reading | | | | | | | | Bye | Walsall | | | | | | | Quarter-finals
| | 28 February 1938 | Queen's Park Rangers | 2 | - | 3 | Watford | 2,095 | Loftus Road, London | | 2 February 1938 | Reading | 3 | - | 1 | Bristol Rovers | 1,392 | Elm Park, Reading | | 16 February 1938 | Swindon Town | 1 | - | 2 | Millwall | 922 | County Ground, Swindon | | 10 January 1938 | Walsall | 1 | - | 2 | Bristol City | 526 | Fellows Park, Walsall | Semi-finals
| | 30 March 1938 | Bristol City | 2 | - | 0 | Millwall | 1,513 | Ashton Gate, Bristol | | 16 March 1938 | Reading | 3 | - | 0 | Watford | 1,629 | Elm Park, Reading | Final
| 1st leg | | 28 September 1938 | Reading | 6 | - | 1 | Bristol City | 1,097 | Elm Park, Reading | | 2nd leg | | 12 October 1938 | Bristol City | 1 | - | 0 | Reading | 718 | Ashton Gate, Bristol | | | (Reading win 6-2 on aggregate) | | |
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