Football League Cup 2023/24, Fifth Round |
 | 19.12.2023 |  | Chelsea | – | Newcastle United | | 1:1 (0:1),
pen. 4:2 |
| London |
Football League Cup 2021/22, Final |
| 27.02.2022 | | Chelsea | – | Liverpool | | 0:0 aet,
pen. 10:11 |
| London |
Football League Cup 2021/22, Fourth Round |
| 26.10.2021 | | Chelsea | – | Southampton | | 1:1 (1:0),
pen. 4:3 |
| London |
Football League Cup 2021/22, Third round |
| 22.09.2021 | | Chelsea | – | Aston Villa | | 1:1 (0:0),
pen. 4:3 |
| London |
Football League Cup 2020/21, Fourth Round |
| 29.09.2020 | | Tottenham Hotspur | – | Chelsea | | 1:1 (0:1),
pen. 5:4 * |
| London |
Football League Cup 2018/19, Final |
| 24.02.2019 | | Chelsea | – | Manchester City | | 0:0 aet,
pen. 3:4 |
| London |
Football League Cup 2017/18, Semifinals |
| 10.01.2018 | | Chelsea | – | Arsenal | | 0:0 |
| London |
Football League Cup 2015/16, Fourth Round |
| 27.10.2015 | | Stoke City | – | Chelsea | | 1:1 aet
(0:0, 1:1),
pen. 5:4 |
| Stoke-on-Trent |
Football League Cup 2014/15, Semifinals |
| 20.01.2015 | | Liverpool | – | Chelsea | | 1:1 (0:1) |
| Liverpool |
Football League Cup 2012/13, Semifinals |
| 23.01.2013 |  | Swansea City | – | Chelsea | | 0:0 |
| Swansea |
Football League Cup 2011/12, Third round |
| 21.09.2011 | | Chelsea | – | Fulham | | 0:0 aet,
pen. 4:3 |
| London |
Football League Cup 2009/10, Fifth Round |
| 02.12.2009 | | Blackburn Rovers | – | Chelsea | | 3:3 aet
(1:0, 2:2),
pen. 4:3 |
| Blackburn |
Football League Cup 2008/09, Fourth Round |
| 12.11.2008 | | Chelsea | – | Burnley | | 1:1 aet
(1:0, 1:1),
pen. 4:5 |
| London |
Football League Cup 2006/07, Semifinals |
| 10.01.2007 | | Wycombe Wanderers | – | Chelsea | | 1:1 (0:1) |
| High Wycombe |
Football League Cup 2005/06, Third round |
| 26.10.2005 | | Chelsea | – | Charlton Athletic | | 1:1 aet
(1:1, 1:1),
pen. 4:5 |
| London |
Football League Cup 2004/05, Semifinals |
| 12.01.2005 | | Chelsea | – | Manchester United | | 0:0 |
| London |
Football League Cup 1997/98, Fifth Round |
| 07.01.1998 | | Ipswich Town | – | Chelsea | | 2:2 aet
(1:2, 2:2),
pen. 1:4 |
| Ipswich |
Football League Cup 1997/98, Third round |
| 15.10.1997 | | Chelsea | – | Blackburn Rovers | | 1:1 aet
(0:0, 1:1),
pen. 4:1 |
| London |
Football League Cup 1995/96, Second round |
| 20.09.1995 | | Stoke City | – | Chelsea | | 0:0 |
| Stoke-on-Trent |
Football League Cup 1993/94, Second round |
| 22.09.1993 | | West Bromwich Albion | – | Chelsea | | 1:1 (1:0) |
| West Bromwich |
Football League Cup 1992/93, Fourth Round |
| 02.12.1992 | | Everton | – | Chelsea | | 2:2 (2:1) |
| Liverpool |
Football League Cup 1991/92, Second round |
| 25.09.1991 | | Chelsea | – | Tranmere Rovers | | 1:1 (0:0) |
| London |
Football League Cup 1990/91, Fifth Round |
| 16.01.1991 | | Chelsea | – | Tottenham Hotspur | | 0:0 |
| London |
Football League Cup 1990/91, Third round |
| 31.10.1990 | | Chelsea | – | Portsmouth | | 0:0 |
| London |
Football League Cup 1989/90, Second round |
| 19.09.1989 | | Chelsea | – | Scarborough | | 1:1 |
| London |
Football League Cup 1988/89, Second round |
| 12.10.1988 | | Chelsea | – | Scunthorpe United | | 2:2 |
| London |
Football League Cup 1985/86, Fifth Round |
| 22.01.1986 | | Queens Park Rangers | – | Chelsea | | 1:1 |
| |
Football League Cup 1985/86, Fourth Round |
| 26.11.1985 | | Chelsea | – | Everton | | 2:2 |
| London |
Football League Cup 1985/86, Third round |
| 29.10.1985 | | Chelsea | – | Fulham | | 1:1 |
| London |
Football League Cup 1985/86, Second round |
| 25.09.1985 | | Mansfield Town | – | Chelsea | | 2:2 |
| |
Football League Cup 1984/85, Fifth Round |
| 30.01.1985 | | Sheffield Wednesday | – | Chelsea | | 4:4 aet * |
| Sheffield |
Football League Cup 1984/85, Fifth Round |
| 28.01.1985 | | Chelsea | – | Sheffield Wednesday | | 1:1 |
| London |
Football League Cup 1984/85, Third round |
| 30.10.1984 | | Walsall | – | Chelsea | | 2:2 |
| |
Football League Cup 1984/85, Second round |
| 09.10.1984 | | Millwall | – | Chelsea | | 1:1 |
| |
Football League Cup 1981/82, Second round |
| 06.10.1981 | | Southampton | – | Chelsea | | 1:1 |
| |
Football League Cup 1980/81, Second round |
| 03.09.1980 | | Chelsea | – | Cardiff City | | 1:1 |
| London |
Football League Cup 1979/80, Second round |
| 28.08.1979 | | Plymouth Argyle | – | Chelsea | | 2:2 |
| |
Football League Cup 1974/75, Third round |
| 16.10.1974 | | Stoke City | – | Chelsea | | 1:1 aet * |
| |
Football League Cup 1974/75, Third round |
| 09.10.1974 | | Chelsea | – | Stoke City | | 2:2 |
| London |
Football League Cup 1972/73, Third round |
| 04.10.1972 | | Derby County | – | Chelsea | | 0:0 |
| |
Football League Cup 1971/72, Semifinals |
| 05.01.1972 | | Tottenham Hotspur | – | Chelsea | | 2:2 |
| London |
Football League Cup 1971/72, Fourth Round |
| 27.10.1971 | | Chelsea | – | Bolton Wanderers | | 1:1 |
| London |
Football League Cup 1971/72, Third round |
| 06.10.1971 | | Nottingham Forest | – | Chelsea | | 1:1 |
| |
Football League Cup 1970/71, Second round |
| 09.09.1970 | | Sheffield Wednesday | – | Chelsea | | 1:1 |
| |
Football League Cup 1969/70, Third round |
| 24.09.1969 | | Leeds United | – | Chelsea | | 1:1 |
| Leeds |
Football League Cup 1968/69, Third round |
| 25.09.1968 | | Chelsea | – | Derby County | | 0:0 |
| London |
Football League Cup 1966/67, Third round |
| 05.10.1966 | | Blackpool | – | Chelsea | | 1:1 |
| |
Football League Cup 1964/65, Final |
| 05.04.1965 | | Leicester City | – | Chelsea | | 0:0 |
| Leicester |
Football League Cup 1964/65, Semifinals |
| 10.02.1965 | | Chelsea | – | Aston Villa | | 1:1 (0:1) |
| London |
Football League Cup 1964/65, Fifth Round |
| 25.11.1964 | | Workington | – | Chelsea | | 2:2 |
| |
