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 | | | John Dick
| | | | | | | | 9 October 1957 | Aldershot | 0 | - | 0 | Millwall | 3,496 | Recreation Ground, Aldershot | | 14 October 1957 | Portsmouth | 4 | - | 1 | Charlton Athletic | | Fratton Park, Portsmouth | | | Johnny Gordon (2), Jack Mansell (2)
| | | | Johnny Summers
| | | | 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 | | | Ron Tindall
| | | | Johnny Doherty, Roy Bentley
| | | | 22 October 1957 | Watford | 4 | - | 1 | Crystal Palace | 2,370 | Vicarage Road, Watford | | | Bryan Atkinson (2), Tony Collins, Tommy McMillan
| | | | George Cooper
| | | | 28 October 1957 | Southampton | 0 | - | 2 | Luton Town | 6,712 | The Dell, Southampton | | | | | | | Gordon Turner, George Cummins
| | | | 30 October 1957 | Brentford | 4 | - | 1 | Arsenal | 13,000 | Griffin Park, London | | | George Francis, Eric Parsons (2), George Bristow
| | | | Cliff Holton
| | | Replay
| | 14 October 1957 | Millwall | 2 | - | 1 | Aldershot | | The Den, London | | | Roy Summersby (2)
| | | | | | | | | | | | | | | | | 6 November 1957 | Reading | 5 | - | 2 | Queen's Park Rangers | 6,377 | Elm Park, Reading | | | Jimmy Whitehouse (3), Jimmy Wheeler, Tommy Dixon
| | | | Pat Kerrins, Les Locke
| | | | Quarter-finals | | 12 November 1957 | Watford | 4 | - | 2 | Fulham | 4,927 | Vicarage Road, Watford | | | Maurice Cook, Bobby Howfield, Jimmy Meadows, Bill Shipwright
| | | | Roy Dwight, Tony Barton
| | | | 25 November 1957 | Millwall | 2 | - | 3 | Portsmouth | | The Den, London | | | John Shepherd
| | | | Ray Crawford (2), Jack Mansell
| | | | 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 | | | John Smith, Vic Keeble, John Dick
| | | | Tommy Dixon (2) Duggie Webb
| | | Replays
| | 29 January 1958 | Luton Town | 7 | - | 1 | Brentford | 4,010 | Kenilworth Road, Luton | | | Gordon Turner (2), George McLeod (2), Jimmy Adam, Allan Brown, John Groves
| | | | Jim Towers
| | | | 29 January 1958 | Reading | 5 | - | 3 | West Ham United | 13,000 | Elm Park, Reading | | | Harry Gunning, Tommy Dixon (2), Ray Reeves, Peter Harrison
| | | | Billy Neville, John Dick, Malcolm Musgrove
| | | Semi-Finals
| | 25 March 1958 | Reading | 3 | - | 3 | Luton Town | 10,881 | Elm Park, Reading | | | Tommy Dixon, Jimmy Wheeler (2)
| | | | Gordon Turner (2, 1 pen.), John Groves
| | | | 31 March 1958 | Watford | 0 | - | 1 | Portsmouth | 4,466 | Vicarage Road, Watford | | | | | | | Derek Dougan
| | | Replay
| | 31 March 1958 | Luton Town | 0 | - | 1 | Reading | 4,606 | Kenilworth Road, Luton | | | | | | | Tommy Dixon
| | | | Final | | 30 April 1958 | Reading | 0 | - | 2 | Portsmouth | 15,000 | Elm Park Reading | | | | | | | Michael Watts, Derek Weddle
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