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 | | | Ron Brett (2), Johnny Byrne, Terry Long
| | | | Jimmy Wheeler, Johnny Walker
| | | | 13 October 1958 | Queen's Park Rangers | 0 | - | 4 | Fulham | 8,497 | Loftus Road, London | | | | | | | John Doherty, Roy Bentley, Mike Johnson, John Key
| | | | 14 October 1958 | Brentford | 3 | - | 2 | Leyton Orient | 6,500 | Griffin Park, London | | | Jim Towers, George Francis, Ken Horne (pen.)
| | | | Sid McClellan, Eddie Lewis
| | | | 15 October 1958 | Aldershot | 2 | - | 3 | Arsenal | 6,000 | Recreation Ground, Aldershot | | | Arthur Tyrer, Derek Price
| | | | Jimmy Bloomfield, Dennis Evans (pen.), Vic Groves
| | | | 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 | | | John Dick (2), Malcolm Musgrove (3)
| | | | Johnny Summers
| | | | 3 November 1958 | Millwall | 6 | - | 1 | Coventry City | 5,283 | The Den, London | | | Ron Heckman (3), Roy Summersby (2), Joe Broadfoot
| | | | Ken Satchwell
| | | | 3 November 1958 | Portsmouth | 0 | - | 2 | Luton Town | 5,066 | Fratton Park, Portsmouth | | | | | | | Gordon Turner (2)
| | | Replay
| | 4 November 1958 | Watford | 2 | - | 3 | Southampton | 8,328 | Vicarage Road, Watford | | | Freddie Bunce, Cliff Holton
| | | | Derek Reeves (2), Jimmy Shields
| | | | Quarter-finals | | 8 December 1958 | Brentford | 1 | - | 2 | Arsenal | 12,500 | Griffin Park, London | | | George Francis
| | | | Dennis Clapton, Gordon Nutt
| | | | 15 December 1958 | West Ham United | 3 | - | 1 | Fulham | 4,500 | Boleyn Ground, London | | | John Bond, Phil Woosnam, Vic Keeble
| | | | John Doherty | | | | 19 January 1959 | Millwall | 1 | - | 1 | Crystal Palace | 5,569 | The Den, London | | | Bob Humphries
| | | | Johnny Byrne | | | | 18 February 1959 | Luton Town | 4 | - | 0 | Southampton | 2,803 | Kenilworth Road, Luton | | | Bob Morton (2), Tony Gregory, George Cummins
| | | | | | | Replay
| | 28 January 1959 | Crystal Palace | 3 | - | 2 | Millwall | 8,831 | Selhurst Park, London | | | | | | | Ray Brady (pen.), Johnny Roche
| | | Semi-Finals
| | 1 April 1959 | Crystal Palace | 1 | - | 0 | Luton Town | 15,731 | Selhurst Park, London | | | Tommy Barnett | | | | | | | | 6 April 1959 | West Ham United | 0 | - | 2 | Arsenal | 15,681 | Boleyn Ground, London | | | | | | | Mel Charles (2) | | | | Final | | 27 April 1959 | Crystal Palace | 1 | - | 2 | Arsenal | 32,000 | Selhurst Park, London | | | Johnny Byrne | | | | Danny Clapton, Mel Charles
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