Southern Professional Floodlit Cup 1957-58 
Winners: Portsmouth Runners-up: Reading Winners from previous season: Luton Town First round
| | 23 September 1957 | West Ham United | 1 | - | 0 | Leyton Orient | 10,000 | Boleyn Ground, London | | 9 October 1957 | Aldershot | 0 | - | 0 | Millwall | 3,496 | Recreation Ground, Aldershot | | 14 October 1957 | Portsmouth | 4 | - | 1 | Charlton Athletic | | Fratton Park, Portsmouth | | 14 October 1957 | Queen's Park Rangers | 0 | - | 0 | Reading | | Loftus Road, London | | 15 October 1957 | Chelsea | 1 | - | 2 | Fulham | 15,056 | Stamford Bridge, London | | 22 October 1957 | Watford | 4 | - | 1 | Crystal Palace | 2,370 | Vicarage Road, Watford | | 28 October 1957 | Southampton | 0 | - | 2 | Luton Town | 6,712 | The Dell, Southampton | | 30 October 1957 | Brentford | 4 | - | 1 | Arsenal | 13,000 | Griffin Park, London | Replay
| | 14 October 1957 | Millwall | 2 | - | 1 | Aldershot | | The Den, London | | 6 November 1957 | Reading | 5 | - | 2 | Queen's Park Rangers | 6,377 | Elm Park, Reading | | Quarter-finals | | 12 November 1957 | Watford | 4 | - | 2 | Fulham | 4,927 | Vicarage Road, Watford | | 25 November 1957 | Millwall | 2 | - | 3 | Portsmouth | | The Den, London | | 10 December 1957 | Brentford | 0 | - | 0 | Luton Town | 4,350 | Griffin Park, London | | 13 January 1958 | West Ham United | 3 | - | 3 | Reading | 5,000 | Boleyn Ground, London | Replays
| | 29 January 1958 | Luton Town | 7 | - | 1 | Brentford | 4,010 | Kenilworth Road, Luton | | 29 January 1958 | Reading | 5 | - | 3 | West Ham United | 13,000 | Elm Park, Reading | Semi-Finals
| | 25 March 1958 | Reading | 3 | - | 3 | Luton Town | 10,881 | Elm Park, Reading | | 31 March 1958 | Watford | 0 | - | 1 | Portsmouth | 4,466 | Vicarage Road, Watford | Replay
| | 31 March 1958 | Luton Town | 0 | - | 1 | Reading | 4,606 | Kenilworth Road, Luton | | Final | | 30 April 1958 | Reading | 0 | - | 2 | Portsmouth | | Elm Park Reading |
|
