Football League Cup 2002/03, Second round |
 | 01.10.2002 |  | Portsmouth | – | Wimbledon | | 1:3 (1:2) |
| Portsmouth |
Football League Cup 2002/03, First Round |
| 10.09.2002 | | Southend United | – | Wimbledon | | 1:4 (0:1) |
| Southend-on-Sea |
Football League Cup 2000/01, Third round |
| 31.10.2000 | | Wimbledon | – | Middlesbrough | | 1:0 (0:0) |
| London |
Football League Cup 2000/01, Second round |
| 26.09.2000 | | Wigan Athletic | – | Wimbledon | | 1:2 (0:1) |
| Wigan |
Football League Cup 1999/00, Fourth Round |
| 30.11.1999 | | Huddersfield Town | – | Wimbledon | | 1:2 aet
(1:0, 1:1) |
| Huddersfield |
Football League Cup 1999/00, Third round |
| 12.10.1999 | | Wimbledon | – | Sunderland | | 3:2 aet
(0:0, 1:1) |
| London |
Football League Cup 1999/00, Second round |
| 21.09.1999 | | Wimbledon | – | Cardiff City |  | 3:1 (0:1) |
| London |
Football League Cup 1998/99, Fifth Round |
| 01.12.1998 | | Wimbledon | – | Chelsea | | 2:1 (1:0) |
| London |
Football League Cup 1998/99, Fourth Round |
| 10.11.1998 | | Bolton Wanderers | – | Wimbledon | | 1:2 (0:1) |
| Bolton |
Football League Cup 1998/99, Third round |
| 28.10.1998 | | Birmingham City | – | Wimbledon | | 1:2 (1:1) |
| Birmingham |
Football League Cup 1998/99, Second round |
| 22.09.1998 | | Wimbledon | – | Portsmouth | | 4:1 aet
(1:1, 2:1) |
| London |
Football League Cup 1997/98, Second round |
| 01.10.1997 | | Millwall | – | Wimbledon | | 1:4 (0:2) |
| London |
Football League Cup 1997/98, Second round |
| 16.09.1997 | | Wimbledon | – | Millwall | | 5:1 (2:1) |
| London |
Football League Cup 1996/97, Fifth Round |
| 08.01.1997 | | Bolton Wanderers | – | Wimbledon | | 0:2 (0:2) |
| Bolton |
Football League Cup 1996/97, Fourth Round |
| 26.11.1996 | | Wimbledon | – | Aston Villa | | 1:0 (1:0) |
| London |
Football League Cup 1996/97, Third round |
| 12.11.1996 | | Luton Town | – | Wimbledon | | 1:2 aet
(1:0, 1:1) * |
| Luton |
Football League Cup 1996/97, Second round |
| 18.09.1996 | | Wimbledon | – | Portsmouth | | 1:0 (0:0) |
| London |
Football League Cup 1994/95, Second round |
| 05.10.1994 | | Torquay United | – | Wimbledon | | 0:1 (0:1) |
| Torquay |
Football League Cup 1994/95, Second round |
| 20.09.1994 | | Wimbledon | – | Torquay United | | 2:0 (2:0) |
| London |
Football League Cup 1993/94, Third round |
| 27.10.1993 | | Wimbledon | – | Newcastle United | | 2:1 (1:1) |
| London |
Football League Cup 1993/94, Second round |
| 05.10.1993 | | Wimbledon | – | Hereford United | | 4:1 (3:0) |
| London |
Football League Cup 1993/94, Second round |
| 22.09.1993 | | Hereford United | – | Wimbledon | | 0:1 (0:1) |
| Hereford |
Football League Cup 1992/93, Second round |
| 22.09.1992 | | Bolton Wanderers | – | Wimbledon | | 1:3 (0:2) |
| Bolton |
Football League Cup 1989/90, Third round |
| 08.11.1989 | | Wimbledon | – | Middlesbrough | | 1:0 * |
| London |
Football League Cup 1989/90, Second round |
| 04.10.1989 | | Wimbledon | – | Port Vale | | 3:0 |
| London |
Football League Cup 1989/90, Second round |
| 18.09.1989 | | Port Vale | – | Wimbledon | | 1:2 |
| Stoke-on-Trent |
Football League Cup 1988/89, Third round |
| 02.11.1988 | | Wimbledon | – | Manchester United | | 2:1 |
| London |
Football League Cup 1988/89, Second round |
| 27.09.1988 | | Barnsley | – | Wimbledon | | 0:2 |
| Barnsley |
Football League Cup 1987/88, Third round |
| 28.10.1987 | | Wimbledon | – | Newcastle United | | 2:1 |
| London |
Football League Cup 1987/88, Second round |
| 06.10.1987 | | Wimbledon | – | Rochdale | | 2:1 |
| London |
Football League Cup 1985/86, Second round |
| 24.09.1985 | | Wimbledon | – | Blackburn Rovers | | 5:0 |
| |
Football League Cup 1984/85, First Round |
| 04.09.1984 | | Wimbledon | – | Portsmouth | | 1:0 |
| |
Football League Cup 1983/84, Third round |
| 08.11.1983 | | Wimbledon | – | Oldham Athletic | | 3:1 |
| |
Football League Cup 1983/84, Second round |
| 04.10.1983 | | Wimbledon | – | Nottingham Forest | | 2:0 |
| |
Football League Cup 1983/84, First Round |
| 13.09.1983 | | Wimbledon | – | Southend United | | 6:4 aet |
| |
Football League Cup 1980/81, Second round |
| 26.08.1980 | | Wimbledon | – | Sheffield Wednesday | | 2:1 |
| |
Football League Cup 1980/81, First Round |
| 12.08.1980 | | Wimbledon | – | Aldershot | | 4:1 |
| |
Football League Cup 1979/80, Third round |
| 02.10.1979 | | Wimbledon | – | Plymouth Argyle | | 1:0 aet * |
| |
Football League Cup 1979/80, First Round |
| 14.08.1979 | | Aldershot | – | Wimbledon | | 1:2 |
| |
Football League Cup 1979/80, First Round |
| 11.08.1979 | | Wimbledon | – | Aldershot | | 4:1 |
| |
Football League Cup 1978/79, First Round |
| 15.08.1978 | | Wimbledon | – | Southend United | | 4:1 |
| |
Football League Cup 1977/78, First Round |
| 16.08.1977 | | Wimbledon | – | Gillingham | | 3:1 |
| |
