Football League Cup 2023/24, Third Round |
 | 26.09.2023 |  | Ipswich Town | – | Wolverhampton Wanderers | | 3:2 (2:2) |
| Ipswich |
Football League Cup 2020/21, Second round |
| 17.09.2020 | | Wolverhampton Wanderers | – | Stoke City | | 0:1 (0:0) * |
| Wolverhampton |
Football League Cup 2019/20, Fourth Round |
| 30.10.2019 | | Aston Villa | – | Wolverhampton Wanderers | | 2:1 (1:0) |
| Birmingham |
Football League Cup 2016/17, Third round |
| 20.09.2016 | | Newcastle United | – | Wolverhampton Wanderers | | 2:0 (2:0) |
| Newcastle upon Tyne |
Football League Cup 2015/16, Third round |
| 22.09.2015 | | Middlesbrough | – | Wolverhampton Wanderers | | 3:0 (1:0) |
| Middlesbrough |
Football League Cup 2014/15, First Round |
| 12.08.2014 | | Wolverhampton Wanderers | – | Northampton Town | | 2:3 (0:0) |
| Wolverhampton |
Football League Cup 2013/14, First Round |
| 06.08.2013 | | Morecambe | – | Wolverhampton Wanderers | | 1:0 (0:0) |
| Morecambe |
Football League Cup 2012/13, Third round |
| 25.09.2012 | | Chelsea | – | Wolverhampton Wanderers | | 6:0 (3:0) |
| London |
Football League Cup 2011/12, Fourth Round |
| 26.10.2011 | | Wolverhampton Wanderers | – | Manchester City | | 2:5 (1:3) |
| Wolverhampton |
Football League Cup 2010/11, Fourth Round |
| 26.10.2010 | | Manchester United | – | Wolverhampton Wanderers | | 3:2 (0:0) |
| Manchester |
Football League Cup 2009/10, Third round |
| 23.09.2009 | | Manchester United | – | Wolverhampton Wanderers | | 1:0 (0:0) |
| Manchester |
Football League Cup 2007/08, Second round |
| 28.08.2007 | | Wolverhampton Wanderers | – | Morecambe | | 1:3 aet
(0:0, 1:1) |
| Wolverhampton |
Football League Cup 2005/06, Second round |
| 20.09.2005 | | Watford | – | Wolverhampton Wanderers | | 2:1 aet
(1:1, 1:1) |
| Watford |
Football League Cup 2003/04, Fourth Round |
| 02.12.2003 | | Arsenal | – | Wolverhampton Wanderers | | 5:1 (1:0) |
| London |
Football League Cup 2001/02, First Round |
| 22.08.2001 | | Wolverhampton Wanderers | – | Swindon Town | | 1:2 (0:0) |
| Wolverhampton |
Football League Cup 2000/01, Third round |
| 01.11.2000 | | Fulham | – | Wolverhampton Wanderers | | 3:2 (0:0) |
| London |
Football League Cup 2000/01, Second round |
| 26.09.2000 | | Grimsby Town | – | Wolverhampton Wanderers | | 3:2 (1:2) |
| Cleethorpes |
Football League Cup 2000/01, First Round |
| 22.08.2000 | | Wolverhampton Wanderers | – | Oxford United | | 0:1 (0:1) |
| Wolverhampton |
Football League Cup 1999/00, First Round |
| 24.08.1999 | | Wolverhampton Wanderers | – | Wycombe Wanderers | | 2:4 (0:2) |
| Wolverhampton |
Football League Cup 1998/99, Second round |
| 22.09.1998 | | Wolverhampton Wanderers | – | AFC Bournemouth | | 1:2 (0:1) |
| Wolverhampton |
Football League Cup 1998/99, First Round |
| 11.08.1998 | | Barnet | – | Wolverhampton Wanderers | | 2:1 (0:0) |
| London |
Football League Cup 1997/98, Third round |
| 14.10.1997 | | Reading | – | Wolverhampton Wanderers | | 4:2 (2:1) |
| Reading |
Football League Cup 1997/98, First Round |
| 27.08.1997 | | Wolverhampton Wanderers | – | Queens Park Rangers | | 1:2 (0:1) |
| Wolverhampton |
Football League Cup 1996/97, First Round |
| 20.08.1996 | | Swindon Town | – | Wolverhampton Wanderers | | 2:0 (1:0) |
| Swindon |
Football League Cup 1995/96, Fifth Round |
| 10.01.1996 | | Aston Villa | – | Wolverhampton Wanderers | | 1:0 (0:0) |
| Birmingham |
Football League Cup 1994/95, Third round |
| 26.10.1994 | | Wolverhampton Wanderers | – | Nottingham Forest | | 2:3 (1:2) |
| Wolverhampton |
Football League Cup 1993/94, Second round |
| 22.09.1993 | | Swindon Town | – | Wolverhampton Wanderers | | 2:0 (1:0) |
| Swindon |
Football League Cup 1992/93, Second round |
| 07.10.1992 | | Wolverhampton Wanderers | – | Notts County | | 0:1 (0:0) |
| Wolverhampton |
Football League Cup 1992/93, Second round |
| 22.09.1992 | | Notts County | – | Wolverhampton Wanderers | | 3:2 (3:1) |
| Nottingham |
Football League Cup 1991/92, Third round |
| 30.10.1991 | | Everton | – | Wolverhampton Wanderers | | 4:1 (2:1) |
| Liverpool |
Football League Cup 1991/92, Second round |
| 08.10.1991 | | Shrewsbury Town | – | Wolverhampton Wanderers | | 3:1 (1:1) |
| Shrewsbury |
Football League Cup 1989/90, Second round |
| 20.09.1989 | | Aston Villa | – | Wolverhampton Wanderers | | 2:1 (1:0) |
| Birmingham |
Football League Cup 1988/89, First Round |
| 06.09.1988 | | Birmingham City | – | Wolverhampton Wanderers | | 1:0 aet |
| Birmingham |
Football League Cup 1987/88, Second round |
| 06.10.1987 | | Wolverhampton Wanderers | – | Manchester City | | 0:2 |
| Wolverhampton |
Football League Cup 1986/87, First Round |
| 26.08.1986 | | Wolverhampton Wanderers | – | Lincoln City | | 1:2 |
| Wolverhampton |
Football League Cup 1985/86, First Round |
| 03.09.1985 | | Wolverhampton Wanderers | – | Walsall | | 0:1 |
| |
Football League Cup 1985/86, First Round |
| 20.08.1985 | | Walsall | – | Wolverhampton Wanderers | | 4:1 |
| |
Football League Cup 1984/85, Third round |
| 06.11.1984 | | Wolverhampton Wanderers | – | Southampton | | 0:2 * |
| |
Football League Cup 1983/84, Second round |
| 25.10.1983 | | Preston North End | – | Wolverhampton Wanderers | | 1:0 |
| |
Football League Cup 1983/84, Second round |
| 04.10.1983 | | Wolverhampton Wanderers | – | Preston North End | | 2:3 |
| |
Football League Cup 1982/83, Second round |
| 27.10.1982 | | Sunderland | – | Wolverhampton Wanderers | | 5:0 |
| Sunderland |
Football League Cup 1981/82, Second round |
| 27.10.1981 | | Wolverhampton Wanderers | – | Aston Villa | | 1:2 (0:1) |
| Wolverhampton |
Football League Cup 1981/82, Second round |
| 07.10.1981 | | Aston Villa | – | Wolverhampton Wanderers | | 3:2 (0:1) |
| Birmingham |
Football League Cup 1980/81, Second round |
| 02.09.1980 | | Wolverhampton Wanderers | – | Cambridge United | | 0:1 |
| |
Football League Cup 1980/81, Second round |
| 26.08.1980 | | Cambridge United | – | Wolverhampton Wanderers | | 3:1 |
| |
Football League Cup 1979/80, Semifinals |
| 22.01.1980 | | Swindon Town | – | Wolverhampton Wanderers | | 2:1 (1:1) |
| Swindon |
Football League Cup 1978/79, Second round |
| 30.08.1978 | | Reading | – | Wolverhampton Wanderers | | 1:0 |
| |
Football League Cup 1977/78, Second round |
| 30.08.1977 | | Wolverhampton Wanderers | – | Luton Town | | 1:3 |
| |
Football League Cup 1976/77, Second round |
| 31.08.1976 | | Wolverhampton Wanderers | – | Sheffield Wednesday | | 1:2 |
| |
Football League Cup 1975/76, Fourth Round |
| 12.11.1975 | | Mansfield Town | – | Wolverhampton Wanderers | | 1:0 |
| |
Football League Cup 1974/75, Second round |
| 11.09.1974 | | Wolverhampton Wanderers | – | Fulham | | 1:3 |
| |
Football League Cup 1972/73, Semifinals |
| 20.12.1972 | | Wolverhampton Wanderers | – | Tottenham Hotspur | | 1:2 |
| |
Football League Cup 1971/72, Second round |
| 08.09.1971 | | Manchester City | – | Wolverhampton Wanderers | | 4:3 |
| Manchester |
Football League Cup 1970/71, Second round |
| 09.09.1970 | | Oxford United | – | Wolverhampton Wanderers | | 1:0 |
| |
Football League Cup 1969/70, Fourth Round |
| 14.10.1969 | | Queens Park Rangers | – | Wolverhampton Wanderers | | 3:1 |
| |
Football League Cup 1968/69, Fourth Round |
| 16.10.1968 | | Blackpool | – | Wolverhampton Wanderers | | 2:1 |
| |
Football League Cup 1967/68, Second round |
| 12.09.1967 | | Huddersfield Town | – | Wolverhampton Wanderers | | 1:0 |
| Huddersfield |
Football League Cup 1966/67, Third round |
| 05.10.1966 | | Fulham | – | Wolverhampton Wanderers | | 5:0 |
| |
