Southern Professional Floodlit Cup 1958-59 
Winners: Arsenal Runners-up: Crystal Palace Winners from previous season: Portsmouth First round
| | 13 October 1958 | Crystal Palace | 4 | - | 2 | Reading | 2,807 | Selhurst Park, London | | 13 October 1958 | Queen's Park Rangers | 2 | - | 4 | Fulham | 8,497 | Loftus Road, London | | 14 October 1958 | Brentford | 3 | - | 2 | Leyton Orient | 6,500 | Griffin Park, London | | 15 October 1958 | Aldershot | 2 | - | 3 | Arsenal | 6,000 | Recreation Ground, Aldershot | | 27 October 1958 | Southampton | 0 | - | 0 | Watford | 5,240 | The Dell, Southampton | | 27 October 1958 | West Ham United | 5 | - | 1 | Charlton Athletic | 8,500 | Boleyn Ground, London | | 3 November 1958 | Millwall | 6 | - | 1 | Coventry City | 5,283 | The Den, London | | 3 November 1958 | Portsmouth | 0 | - | 2 | Luton Town | 5,066 | Fratton Park, Portsmouth | Replay
| | 4 November 1958 | Watford | 2 | - | 3 | Southampton | 8,328 | Vicarage Road, Watford | | Quarter-finals | | 8 December 1958 | Brentford | 1 | - | 2 | Arsenal | 12,500 | Griffin Park, London | | 15 December 1958 | West Ham United | 3 | - | 1 | Fulham | 4,500 | Boleyn Ground, London | | 19 January 1959 | Millwall | 1 | - | 1 | Crystal Palace | 5,569 | The Den, London | | 18 February 1959 | Luton Town | 4 | - | 0 | Southampton | 2,803 | Kenilworth Road, Luton | Replay
| | 28 January 1959 | Crystal Palace | 3 | - | 2 | Millwall | 8,831 | Selhurst Park, London | Semi-Finals
| | 1 April 1959 | Crystal Palace | 1 | - | 0 | Luton Town | 15,731 | Selhurst Park, London | | 6 April 1959 | West Ham United | 0 | - | 2 | Arsenal | 15,681 | Boleyn Ground, London | | Final | | 27 April 1959 | Crystal Palace | 0 | - | 2 | Arsenal | 32,000 | Selhurst Park, London |
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