Football League Cup 2023/24, Final |
 | 25.02.2024 | | Chelsea | – | Liverpool | | 0:1 aet
(0:0, 0:0) |
| London |
Football League Cup 2023/24, Semifinals |
| 09.01.2024 | | Middlesbrough | – | Chelsea | | 1:0 (1:0) |
| Middlesbrough |
Football League Cup 2022/23, Third Round |
| 09.11.2022 | | Manchester City | – | Chelsea | | 2:0 (0:0) |
| Manchester |
Football League Cup 2019/20, Fourth Round |
| 30.10.2019 | | Chelsea | – | Manchester United | | 1:2 (0:1) |
| London |
Football League Cup 2018/19, Semifinals |
| 08.01.2019 | | Tottenham Hotspur | – | Chelsea | | 1:0 (1:0) |
| London |
Football League Cup 2017/18, Semifinals |
| 24.01.2018 | | Arsenal | – | Chelsea | | 2:1 (1:1) |
| London |
Football League Cup 2016/17, Fourth Round |
| 26.10.2016 | | West Ham United | – | Chelsea | | 2:1 (1:0) |
 | London |
Football League Cup 2013/14, Fifth Round |
| 17.12.2013 | | Sunderland | – | Chelsea | | 2:1 aet
(0:0, 1:1) |
| Sunderland |
Football League Cup 2012/13, Semifinals |
| 09.01.2013 | | Chelsea | – | Swansea City | | 0:2 (0:1) |
| London |
Football League Cup 2011/12, Fifth Round |
| 29.11.2011 | | Chelsea | – | Liverpool | | 0:2 (0:0) |
| London |
Football League Cup 2010/11, Third round |
| 22.09.2010 | | Chelsea | – | Newcastle United | | 3:4 (1:2) |
| London |
Football League Cup 2007/08, Final |
| 24.02.2008 | | Chelsea | – | Tottenham Hotspur | | 1:2 aet
(1:0, 1:1) |
| London |
Football League Cup 2003/04, Fifth Round |
| 17.12.2003 | | Aston Villa | – | Chelsea | | 2:1 (1:0) |
| Birmingham |
Football League Cup 2002/03, Fifth Round |
| 17.12.2002 | | Manchester United | – | Chelsea | | 1:0 (0:0) |
| Manchester |
Football League Cup 2001/02, Semifinals |
| 23.01.2002 | | Tottenham Hotspur | – | Chelsea | | 5:1 (2:0) |
| London |
Football League Cup 2000/01, Third round |
| 01.11.2000 | | Liverpool | – | Chelsea | | 2:1 aet
(1:1, 1:1) |
| Liverpool |
Football League Cup 1999/00, Third round |
| 13.10.1999 | | Chelsea | – | Huddersfield Town | | 0:1 (0:0) |
| London |
Football League Cup 1998/99, Fifth Round |
| 01.12.1998 | | Wimbledon | – | Chelsea | | 2:1 (1:0) |
| London |
Football League Cup 1997/98, Semifinals |
| 28.01.1998 | | Arsenal | – | Chelsea | | 2:1 (1:0) |
| London |
Football League Cup 1996/97, Third round |
| 22.10.1996 | | Bolton Wanderers | – | Chelsea | | 2:1 (2:1) |
| Bolton |
Football League Cup 1996/97, Second round |
| 25.09.1996 | | Chelsea | – | Blackpool | | 1:3 (0:1) |
| London |
Football League Cup 1995/96, Second round |
| 04.10.1995 | | Chelsea | – | Stoke City | | 0:1 (0:0) |
| London |
Football League Cup 1994/95, Third round |
| 26.10.1994 | | West Ham United | – | Chelsea | | 1:0 (1:0) |
| London |
Football League Cup 1993/94, Third round |
| 26.10.1993 | | Manchester City | – | Chelsea | | 1:0 (0:0) |
| Manchester |
Football League Cup 1992/93, Fifth Round |
| 06.01.1993 | | Crystal Palace | – | Chelsea | | 3:1 (2:1) |
| London |
Football League Cup 1991/92, Second round |
| 08.10.1991 | | Tranmere Rovers | – | Chelsea | | 3:1 aet |
| Birkenhead |
Football League Cup 1990/91, Semifinals |
| 27.02.1991 | | Sheffield Wednesday | – | Chelsea | | 3:1 (2:0) |
| Sheffield |
Football League Cup 1990/91, Semifinals |
| 24.02.1991 | | Chelsea | – | Sheffield Wednesday | | 0:2 (0:0) |
| London |
Football League Cup 1989/90, Second round |
| 04.10.1989 | | Scarborough | – | Chelsea | | 3:2 aet |
| Scarborough |
Football League Cup 1988/89, Second round |
| 27.09.1988 | | Scunthorpe United | – | Chelsea | | 4:1 |
| Scunthorpe |
Football League Cup 1987/88, Second round |
| 23.09.1987 | | Reading | – | Chelsea | | 3:1 |
| Reading |
Football League Cup 1986/87, Third round |
| 28.10.1986 | | Cardiff City | – | Chelsea | | 2:1 |
| Cardiff |
Football League Cup 1986/87, Second round |
| 23.09.1986 | | York City | – | Chelsea | | 1:0 |
| York |
Football League Cup 1985/86, Fifth Round |
| 29.01.1986 | | Chelsea | – | Queens Park Rangers | | 0:2 * |
| London |
Football League Cup 1984/85, Semifinals |
| 04.03.1985 | | Chelsea | – | Sunderland | | 2:3 |
| London |
Football League Cup 1984/85, Semifinals |
| 13.02.1985 | | Sunderland | – | Chelsea | | 2:0 |
| Sunderland |
Football League Cup 1983/84, Third round |
| 09.11.1983 | | Chelsea | – | West Bromwich Albion | | 0:1 |
| London |
Football League Cup 1983/84, Second round |
| 25.10.1983 | | Chelsea | – | Leicester City | | 0:2 aet
(0:2),
pen. 4:3 |
| London |
Football League Cup 1982/83, Third round |
| 09.11.1982 | | Notts County | – | Chelsea | | 2:0 |
| |
Football League Cup 1981/82, Third round |
| 11.11.1981 | | Wigan Athletic | – | Chelsea | | 4:2 |
| Wigan |
Football League Cup 1980/81, Second round |
| 27.08.1980 | | Cardiff City | – | Chelsea | | 1:0 |
| |
Football League Cup 1979/80, Second round |
| 04.09.1979 | | Chelsea | – | Plymouth Argyle | | 1:2 |
| London |
Football League Cup 1978/79, Second round |
| 29.08.1978 | | Bolton Wanderers | – | Chelsea | | 2:1 |
| Bolton |
Football League Cup 1977/78, Second round |
| 30.08.1977 | | Liverpool | – | Chelsea | | 2:0 |
| Liverpool |
Football League Cup 1976/77, Fourth Round |
| 26.10.1976 | | Arsenal | – | Chelsea | | 2:1 |
| London |
Football League Cup 1975/76, Second round |
| 10.09.1975 | | Crewe Alexandra | – | Chelsea | | 1:0 |
| |
Football League Cup 1974/75, Third round |
| 22.10.1974 | | Stoke City | – | Chelsea | | 6:2 * |
| Stoke-on-Trent |
Football League Cup 1973/74, Second round |
| 08.10.1973 | | Stoke City | – | Chelsea | | 1:0 |
| |
Football League Cup 1972/73, Semifinals |
| 03.01.1973 | | Norwich City | – | Chelsea | | 1:0 |
| |
Football League Cup 1972/73, Semifinals |
| 13.12.1972 | | Chelsea | – | Norwich City | | 0:2 |
| London |
Football League Cup 1971/72, Final |
| 04.03.1972 | | Stoke City | – | Chelsea | | 2:1 (1:1) |
| London |
Football League Cup 1970/71, Fourth Round |
| 28.10.1970 | | Manchester United | – | Chelsea | | 2:1 |
| Manchester |
Football League Cup 1969/70, Fourth Round |
| 14.10.1969 | | Carlisle United | – | Chelsea | | 1:0 |
| |
Football League Cup 1968/69, Third round |
| 02.10.1968 | | Derby County | – | Chelsea | | 3:1 * |
| |
Football League Cup 1967/68, Second round |
| 13.09.1967 | | Middlesbrough | – | Chelsea | | 2:1 |
| Middlesbrough |
Football League Cup 1966/67, Third round |
| 17.10.1966 | | Chelsea | – | Blackpool | | 1:3 * |
| London |
Football League Cup 1963/64, Second round |
| 25.09.1963 | | Swindon Town | – | Chelsea | | 3:0 |
| |
Football League Cup 1960/61, Fourth Round |
| 14.12.1960 | | Portsmouth | – | Chelsea | | 1:0 |
| Portsmouth |
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