Football League Cup 2024/25, Third Round |
| 24.09.2024 | | Chelsea | | Barrow | | 5:0 (3:0) |
| London |
Football League Cup 2023/24, Semifinals |
| 23.01.2024 | | Chelsea | | Middlesbrough | | 6:1 (4:0) |
| London |
Football League Cup 2023/24, Fourth Round |
| 01.11.2023 | | Chelsea | | Blackburn Rovers | | 2:0 (1:0) |
| London |
Football League Cup 2023/24, Third Round |
| 27.09.2023 | | Chelsea | | Brighton & Hove Albion | | 1:0 (0:0) |
| London |
Football League Cup 2023/24, Second Round |
| 30.08.2023 | | Chelsea | | AFC Wimbledon | | 2:1 (1:1) |
| London |
Football League Cup 2021/22, Semifinals |
| 12.01.2022 | | Tottenham Hotspur | | Chelsea | | 0:1 (0:1) |
| London |
Football League Cup 2021/22, Semifinals |
| 05.01.2022 | | Chelsea | | Tottenham Hotspur | | 2:0 (2:0) |
| London |
Football League Cup 2021/22, Fifth Round |
| 22.12.2021 | | Brentford | | Chelsea | | 0:2 (0:0) |
| Brentford |
Football League Cup 2020/21, Third round |
| 23.09.2020 | | Chelsea | | Barnsley | | 6:0 (2:0) * |
| London |
Football League Cup 2019/20, Third round |
| 25.09.2019 | | Chelsea | | Grimsby Town | | 7:1 (3:1) |
| London |
Football League Cup 2018/19, Semifinals |
| 24.01.2019 | | Chelsea | | Tottenham Hotspur | | 2:1 (2:0), pen. 4:2 |
| London |
Football League Cup 2018/19, Fifth Round |
| 19.12.2018 | | Chelsea | | AFC Bournemouth | | 1:0 (0:0) |
| London |
Football League Cup 2018/19, Fourth Round |
| 31.10.2018 | | Chelsea | | Derby County | | 3:2 (3:2) |
| London |
Football League Cup 2018/19, Third round |
| 26.09.2018 | | Liverpool | | Chelsea | | 1:2 (0:0) |
| Liverpool |
Football League Cup 2017/18, Fifth Round |
| 20.12.2017 | | Chelsea | | AFC Bournemouth | | 2:1 (1:0) |
| London |
Football League Cup 2017/18, Fourth Round |
| 25.10.2017 | | Chelsea | | Everton | | 2:1 (1:0) |
| London |
Football League Cup 2017/18, Third round |
| 20.09.2017 | | Chelsea | | Nottingham Forest | | 5:1 (3:0) |
| London |
Football League Cup 2016/17, Third round |
| 20.09.2016 | | Leicester City | | Chelsea | | 2:4 aet (2:1, 2:2) |
| Leicester |
Football League Cup 2016/17, Second round |
| 23.08.2016 | | Chelsea | | Bristol Rovers | | 3:2 (3:1) |
| London |
Football League Cup 2015/16, Third round |
| 23.09.2015 | | Walsall | | Chelsea | | 1:4 (1:2) |
| Walsall |
Football League Cup 2014/15, Final |
| 01.03.2015 | | Chelsea | | Tottenham Hotspur | | 2:0 (1:0) |
| London |
Football League Cup 2014/15, Semifinals |
| 27.01.2015 | | Chelsea | | Liverpool | | 1:0 aet (0:0) |
| London |
Football League Cup 2014/15, Fifth Round |
| 16.12.2014 | | Derby County | | Chelsea | | 1:3 (0:1) |
| Derby |
Football League Cup 2014/15, Fourth Round |
| 28.10.2014 | | Shrewsbury Town | | Chelsea | | 1:2 (0:0) |
| Shrewsbury |
Football League Cup 2014/15, Third round |
| 24.09.2014 | | Chelsea | | Bolton Wanderers | | 2:1 (1:1) |
| London |
Football League Cup 2013/14, Fourth Round |
| 29.10.2013 | | Arsenal | | Chelsea | | 0:2 (0:1) |
| London |
Football League Cup 2013/14, Third round |
| 24.09.2013 | | Swindon Town | | Chelsea | | 0:2 (0:2) |
| Swindon |
Football League Cup 2012/13, Fifth Round |
| 19.12.2012 | | Leeds United | | Chelsea | | 1:5 (1:0) |
| Leeds |
Football League Cup 2012/13, Fourth Round |
| 31.10.2012 | | Chelsea | | Manchester United | | 5:4 aet (1:2, 3:3) |
| London |
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 | | Everton | | Chelsea | | 1:2 aet (0:1, 1:1) |
| Liverpool |
Football League Cup 2009/10, Fourth Round |
| 28.10.2009 | | Chelsea | | Bolton Wanderers | | 4:0 (2:0) |
| London |
Football League Cup 2009/10, Third round |
| 23.09.2009 | | Chelsea | | Queens Park Rangers | | 1:0 (0:0) |
| London |
Football League Cup 2008/09, Third round |
| 24.09.2008 | | Portsmouth | | Chelsea | | 0:4 (0:2) |
| Portsmouth |
Football League Cup 2007/08, Semifinals |
| 23.01.2008 | | Everton | | Chelsea | | 0:1 (0:0) |
| Liverpool |
Football League Cup 2007/08, Semifinals |
| 08.01.2008 | | Chelsea | | Everton | | 2:1 (1:0) |
| London |
Football League Cup 2007/08, Fifth Round |
| 19.12.2007 | | Chelsea | | Liverpool | | 2:0 (0:0) |
| London |
Football League Cup 2007/08, Fourth Round |
| 31.10.2007 | | Chelsea | | Leicester City | | 4:3 (2:1) |
| London |
Football League Cup 2007/08, Third round |
| 26.09.2007 | | Hull City | | Chelsea | | 0:4 (0:1) |
| Kingston upon Hull |
Football League Cup 2006/07, Final |
| 25.02.2007 | | Arsenal | | Chelsea | | 1:2 (1:1) |
| Cardiff |
Football League Cup 2006/07, Semifinals |
| 23.01.2007 | | Chelsea | | Wycombe Wanderers | | 4:0 (2:0) |
| London |
Football League Cup 2006/07, Fifth Round |
| 20.12.2006 | | Newcastle United | | Chelsea | | 0:1 (0:0) |
| Newcastle upon Tyne |
Football League Cup 2006/07, Fourth Round |
| 08.11.2006 | | Chelsea | | Aston Villa | | 4:0 (1:0) |
| London |
Football League Cup 2006/07, Third round |
| 25.10.2006 | | Blackburn Rovers | | Chelsea | | 0:2 (0:0) |
| Blackburn |
Football League Cup 2004/05, Final |
| 27.02.2005 | | Liverpool | | Chelsea | | 2:3 aet (1:0, 1:1) |
| Cardiff |
Football League Cup 2004/05, Semifinals |
| 26.01.2005 | | Manchester United | | Chelsea | | 1:2 (0:1) |
| Manchester |
Football League Cup 2004/05, Fifth Round |
| 30.11.2004 | | Fulham | | Chelsea | | 1:2 (0:0) |
| London |
Football League Cup 2004/05, Fourth Round |
| 10.11.2004 | | Newcastle United | | Chelsea | | 0:2 aet (0:0) |
| Newcastle upon Tyne |
Football League Cup 2004/05, Third round |
| 27.10.2004 | | Chelsea | | West Ham United | | 1:0 (0:0) |
| London |
Football League Cup 2003/04, Fourth Round |
| 03.12.2003 | | Reading | | Chelsea | | 0:1 (0:0) |
| Reading |
Football League Cup 2003/04, Third round |
| 29.10.2003 | | Chelsea | | Notts County | | 4:2 (2:1) |
| London |
Football League Cup 2002/03, Fourth Round |
| 04.12.2002 | | Chelsea | | Everton | | 4:1 (2:0) |
| London |
Football League Cup 2002/03, Third round |
| 06.11.2002 | | Chelsea | | Gillingham | | 2:1 (1:0) |
| London |
Football League Cup 2001/02, Semifinals |
| 09.01.2002 | | Chelsea | | Tottenham Hotspur | | 2:1 (1:0) |
| London |
Football League Cup 2001/02, Fifth Round |
| 12.12.2001 | | Chelsea | | Newcastle United | | 1:0 (0:0) |
| London |
Football League Cup 2001/02, Fourth Round |
| 28.11.2001 | | Leeds United | | Chelsea | | 0:2 (0:0) |
| Leeds |
Football League Cup 2001/02, Third round |
| 09.10.2001 | | Coventry City | | Chelsea | | 0:2 (0:0) |
| Coventry |
Football League Cup 1998/99, Fourth Round |
| 11.11.1998 | | Arsenal | | Chelsea | | 0:5 (0:1) |
| London |
Football League Cup 1998/99, Third round |
| 28.10.1998 | | Chelsea | | Aston Villa | | 4:1 (1:1) |
| London |
Football League Cup 1997/98, Final |
| 29.03.1998 | | Chelsea | | Middlesbrough | | 2:0 aet (0:0) |
| London |
Football League Cup 1997/98, Semifinals |
| 18.02.1998 | | Chelsea | | Arsenal | | 3:1 (1:0) |
| London |
Football League Cup 1997/98, Fourth Round |
| 19.11.1997 | | Chelsea | | Southampton | | 2:1 aet (0:0, 1:1) |
| London |
Football League Cup 1996/97, Second round |
| 18.09.1996 | | Blackpool | | Chelsea | | 1:4 (1:1) |
| Blackpool |
Football League Cup 1994/95, Second round |
| 04.10.1994 | | Bournemouth | | Chelsea | | 0:1 (0:0) |
| Bournemouth |
Football League Cup 1994/95, Second round |
| 21.09.1994 | | Chelsea | | Bournemouth | | 1:0 (1:0) |
| London |
Football League Cup 1993/94, Second round |
| 06.10.1993 | | Chelsea | | West Bromwich Albion | | 2:1 (1:1) |
| London |
Football League Cup 1992/93, Fourth Round |
| 16.12.1992 | | Chelsea | | Everton | | 1:0 (1:0) * |
| London |
Football League Cup 1992/93, Third round |
| 28.10.1992 | | Chelsea | | Newcastle United | | 2:1 (0:0) |
| London |
Football League Cup 1992/93, Second round |
| 07.10.1992 | | Chelsea | | Walsall | | 1:0 (0:0) |
| London |
Football League Cup 1992/93, Second round |
| 23.09.1992 | | Walsall | | Chelsea | | 0:3 (0:2) |
| Walsall |
Football League Cup 1990/91, Fifth Round |
| 23.01.1991 | | Tottenham Hotspur | | Chelsea | | 0:3 (0:1) * |
| London |
Football League Cup 1990/91, Fourth Round |
| 28.11.1990 | | Oxford United | | Chelsea | | 1:2 |
| Oxford |
Football League Cup 1990/91, Third round |
| 06.11.1990 | | Portsmouth | | Chelsea | | 2:3 * |
| Portsmouth |
Football League Cup 1990/91, Second round |
| 10.10.1990 | | Chelsea | | Walsall | | 4:1 |
| London |
Football League Cup 1990/91, Second round |
| 26.09.1990 | | Walsall | | Chelsea | | 0:5 |
| Walsall |
Football League Cup 1987/88, Second round |
| 07.10.1987 | | Chelsea | | Reading | | 3:2 |
| London |
Football League Cup 1986/87, Second round |
| 08.10.1986 | | Chelsea | | York City | | 3:0 |
| London |
Football League Cup 1985/86, Fourth Round |
| 10.12.1985 | | Everton | | Chelsea | | 1:2 * |
| Liverpool |
Football League Cup 1985/86, Third round |
| 06.11.1985 | | Fulham | | Chelsea | | 0:1 * |
| London |
Football League Cup 1985/86, Second round |
| 09.10.1985 | | Chelsea | | Mansfield Town | | 2:0 |
| London |
Football League Cup 1984/85, Fifth Round |
| 06.02.1985 | | Chelsea | | Sheffield Wednesday | | 2:1 * |
| London |
Football League Cup 1984/85, Fourth Round |
| 21.11.1984 | | Chelsea | | Manchester City | | 4:1 |
| London |
Football League Cup 1984/85, Third round |
| 06.11.1984 | | Chelsea | | Walsall | | 3:0 * |
| London |
Football League Cup 1984/85, Second round |
| 26.09.1984 | | Chelsea | | Millwall | | 3:1 |
| London |
Football League Cup 1983/84, Second round |
| 05.10.1983 | | Leicester City | | Chelsea | | 0:2 |
| |
Football League Cup 1983/84, First Round |
| 13.09.1983 | | Chelsea | | Gillingham | | 4:0 |
| London |
Football League Cup 1983/84, First Round |
| 30.08.1983 | | Gillingham | | Chelsea | | 1:2 |
| |
Football League Cup 1982/83, Second round |
| 27.10.1982 | | Tranmere Rovers | | Chelsea | | 1:2 |
| |
Football League Cup 1982/83, Second round |
| 06.10.1982 | | Chelsea | | Tranmere Rovers | | 3:1 |
| London |
Football League Cup 1981/82, Second round |
| 28.10.1981 | | Chelsea | | Southampton | | 2:1 aet |
| London |
Football League Cup 1976/77, Third round |
| 20.09.1976 | | Chelsea | | Huddersfield Town | | 2:0 |
| London |
Football League Cup 1976/77, Second round |
| 01.09.1976 | | Chelsea | | Sheffield United | | 3:1 |
| London |
Football League Cup 1974/75, Second round |
| 11.09.1974 | | Chelsea | | Newport County | | 4:2 |
| London |
Football League Cup 1972/73, Fifth Round |
| 22.11.1972 | | Chelsea | | Notts County | | 3:1 |
| London |
Football League Cup 1972/73, Fourth Round |
| 31.10.1972 | | Bury | | Chelsea | | 0:1 |
| |
Football League Cup 1972/73, Third round |
| 09.10.1972 | | Chelsea | | Derby County | | 3:2 * |
| London |
Football League Cup 1972/73, Second round |
| 06.09.1972 | | Southend United | | Chelsea | | 0:1 |
| |
Football League Cup 1971/72, Semifinals |
| 22.12.1971 | | Chelsea | | Tottenham Hotspur | | 3:2 |
| London |
Football League Cup 1971/72, Fifth Round |
| 17.11.1971 | | Norwich City | | Chelsea | | 0:1 |
| |
Football League Cup 1971/72, Fourth Round |
| 08.11.1971 | | Bolton Wanderers | | Chelsea | | 0:6 * |
| Bolton |
Football League Cup 1971/72, Third round |
| 11.10.1971 | | Chelsea | | Nottingham Forest | | 2:1 * |
| London |
Football League Cup 1971/72, Second round |
| 08.09.1971 | | Chelsea | | Plymouth Argyle | | 2:0 |
| London |
Football League Cup 1970/71, Third round |
| 07.10.1970 | | Chelsea | | Middlesbrough | | 3:2 |
| London |
Football League Cup 1970/71, Second round |
| 22.09.1970 | | Chelsea | | Sheffield Wednesday | | 2:1 * |
| London |
Football League Cup 1969/70, Third round |
| 06.10.1969 | | Chelsea | | Leeds United | | 2:0 * |
| London |
Football League Cup 1969/70, Second round |
| 02.09.1969 | | Coventry City | | Chelsea | | 0:1 |
| |
Football League Cup 1968/69, Second round |
| 03.09.1968 | | Birmingham City | | Chelsea | | 0:1 |
| Birmingham |
Football League Cup 1966/67, Second round |
| 14.09.1966 | | Chelsea | | Charlton Athletic | | 5:2 |
| London |
Football League Cup 1964/65, Final |
| 15.03.1965 | | Chelsea | | Leicester City | | 3:2 |
| London |
Football League Cup 1964/65, Semifinals |
| 20.01.1965 | | Aston Villa | | Chelsea | | 2:3 (0:2) |
| Birmingham |
Football League Cup 1964/65, Fifth Round |
| 16.12.1964 | | Chelsea | | Workington | | 2:0 * |
| London |
Football League Cup 1964/65, Fourth Round |
| 11.11.1964 | | Chelsea | | Swansea Town | | 3:2 |
| London |
Football League Cup 1964/65, Third round |
| 26.10.1964 | | Chelsea | | Notts County | | 4:0 |
| London |
Football League Cup 1964/65, Second round |
| 23.09.1964 | | Birmingham City | | Chelsea | | 0:3 |
| Birmingham |
Football League Cup 1960/61, Third round |
| 16.11.1960 | | Doncaster Rovers | | Chelsea | | 0:7 |
| |
Football League Cup 1960/61, Second round |
| 24.10.1960 | | Chelsea | | Workington | | 4:2 |
| London |
Football League Cup 1960/61, First Round |
| 10.10.1960 | | Millwall | | Chelsea | | 1:7 |
| London |