Division Three (South) Cup 1936-37 Trophy shared: Millwall & Watford Winners from previous season: Coventry City First round
| 30 September 1936 | Bristol City | 0 | - | 2 | Gillingham | 1,150 | Ashton Gate, Bristol | 30 September 1936 | Crystal Palace | 3 | - | 2 | Brighton & Hove Albion | 2,822 | Selhurst Park, London | 30 September 1936 | Luton Town | 3 | - | 1 | Bournemouth & Boscombe Athletic | 2,527 | Kenilworth Road, Luton | 5 October 1936 | Millwall | 5 | - | 2 | Walsall | 3,000 | The Den, London | 1 October 1936 | Newport County | 1 | - | 4 | Watford | 1,102 | Somerton Park, Newport | 7 October 1936 | Reading | 2 | - | 1 | Queen's Park Rangers | 7,800 | Elm Park, Reading | 30 September 1936 | Swindon Town | 0 | - | 3 | Bristol Rovers | 1,800 | County Ground, Swindon | 30 September 1936 | Torquay United | 5 | - | 0 | Northampton Town | | Plainmoor, Torquay | Bye | Aldershot | | | | | | | Bye | Cardiff City | | | | | | | Bye | Exeter City | | | | | | | Bye | Clapton Orient | | | | | | | Bye | Notts County | | | | | | | Bye | Southend United | | | | | | | Second round
| 28 October 1936 | Exeter City | 1 | - | 0 | Cardiff City | 3,000 | St James's Park, Exeter | 28 October 1936 | Luton Town | 1 | - | 0 | Aldershot | 1,660 | Kenilworth Road, Luton | 21 October 1936 | Notts County | 3 | - | 2 | Reading | 3,212 | Meadow Lane, Nottingham | 28 October 1936 | Southend United | 0 | - | 2 | Clapton Orient | 2,068 | Southend Stadium, Southend | 21 October 1936 | Torquay United | 1 | - | 0 | Crystal Palace | | Plainmoor, Torquay | 28 October 1936 | Watford | 3 | - | 2 | Gillingham | 4,201 | Vicarage Road, Watford | Bye | Bristol Rovers | | | | | | | Bye | Millwall | | | | | | | Quarter-finals
| 11 November 1936 | Bristol Rovers | 0 | - | 1 | Watford | 1,000 | Eastville, Bristol | 11 November 1936 | Luton Town | 2 | - | 4 | Notts County | 1,500 | Kenilworth Road, Luton | 16 November 1936 | Millwall | 3 | - | 2 | Clapton Orient | 4,000 | The Den, London | 11 November 1936 | Torquay United | 2 | - | 1 | Exeter City | 1,000 | Plainmoor, Torquay | Semi-finals
| 26 April 1937 | Notts County | 1 | - | 1 | Watford | 1,300 | Meadow Lane, Nottingham | 21 April 1937 | Torquay United | 2 | - | 2 | Millwall | 2,000 | Plainmoor, Torquay | Replays
| 13 September 1937 | Watford | 8 | - | 3 | Notts County | 1,065 | Vicarage Road, Watford | 29 April 1937 | Millwall | 5 | - | 0 | Torquay United | 3,000 | The Den, London | Final
| 1st leg | 29 September 1937 | Watford | 2 | - | 2 | Millwall | 2,714 | Vicarage Road, Watford | 2nd leg | 18 October 1937 | Millwall | 1 | - | 1 | Watford | 3,368 | The Den, London | | (1-1 on aggregate, trophy shared) | | |
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