Football League Cup 2023/24, Second Round |
 | 29.08.2023 |  | Bolton Wanderers | – | Middlesbrough | | 1:3 (1:1) |
| Bolton |
Football League Cup 2022/23, Second Round |
| 23.08.2022 | | Bolton Wanderers | – | Aston Villa | | 1:4 (1:1) |
| Bolton |
Football League Cup 2020/21, First Round |
| 05.09.2020 | | Bolton Wanderers | – | Bradford City | | 1:2 (0:1) * |
| Bolton |
Football League Cup 2019/20, First Round |
| 13.08.2019 | | Rochdale | – | Bolton Wanderers | | 5:2 (1:1) |
| Rochdale |
Football League Cup 2018/19, First Round |
| 14.08.2018 | | Leeds United | – | Bolton Wanderers | | 2:1 (2:0) |
| Leeds |
Football League Cup 2017/18, Third round |
| 19.09.2017 | | West Ham United | – | Bolton Wanderers | | 3:0 (2:0) |
| London |
Football League Cup 2016/17, First Round |
| 09.08.2016 | | Blackpool | – | Bolton Wanderers | | 4:2 aet
(0:1, 2:2) |
| Blackpool |
Football League Cup 2015/16, First Round |
| 11.08.2015 | | Bolton Wanderers | – | Burton Albion | | 0:1 (0:0) |
| Bolton |
Football League Cup 2014/15, Third round |
| 24.09.2014 | | Chelsea | – | Bolton Wanderers | | 2:1 (1:1) |
| London |
Football League Cup 2012/13, Second round |
| 28.08.2012 | | Crawley Town | – | Bolton Wanderers | | 2:1 (0:1) |
| Crawley |
Football League Cup 2011/12, Fourth Round |
| 25.10.2011 | | Arsenal | – | Bolton Wanderers | | 2:1 (0:0) |
| London |
Football League Cup 2010/11, Third round |
| 21.09.2010 | | Burnley | – | Bolton Wanderers | | 1:0 (1:0) |
| Burnley |
Football League Cup 2009/10, Fourth Round |
| 28.10.2009 | | Chelsea | – | Bolton Wanderers | | 4:0 (2:0) |
| London |
Football League Cup 2008/09, Second round |
| 26.08.2008 | | Bolton Wanderers | – | Northampton Town | | 1:2 (0:2) |
| Bolton |
Football League Cup 2007/08, Fourth Round |
| 31.10.2007 | | Bolton Wanderers | – | Manchester City | | 0:1 (0:0) |
| Bolton |
Football League Cup 2006/07, Third round |
| 25.10.2006 | | Charlton Athletic | – | Bolton Wanderers | | 1:0 (1:0) |
| London |
Football League Cup 2005/06, Fifth Round |
| 20.12.2005 | | Wigan Athletic | – | Bolton Wanderers | | 2:0 (2:0) |
| Wigan |
Football League Cup 2004/05, Third round |
| 27.10.2004 | | Bolton Wanderers | – | Tottenham Hotspur | | 3:4 aet
(1:1, 2:2) |
| Bolton |
Football League Cup 2003/04, Final |
| 29.02.2004 | | Bolton Wanderers | – | Middlesbrough | | 1:2 (1:2) |
| Cardiff |
Football League Cup 2003/04, Semifinals |
| 27.01.2004 | | Aston Villa | – | Bolton Wanderers | | 2:0 (1:0) |
| Birmingham |
Football League Cup 2002/03, Second round |
| 02.10.2002 | | Bolton Wanderers | – | Bury | | 0:1 (0:0) |
| Bolton |
Football League Cup 2001/02, Fifth Round |
| 11.12.2001 | | Tottenham Hotspur | – | Bolton Wanderers | | 6:0 (4:0) |
| London |
Football League Cup 2000/01, First Round |
| 05.09.2000 | | Macclesfield Town | – | Bolton Wanderers | | 3:1 (2:0) |
| Macclesfield |
Football League Cup 1999/00, Semifinals |
| 26.01.2000 | | Tranmere Rovers | – | Bolton Wanderers | | 3:0 (2:0) |
| Birkenhead |
Football League Cup 1999/00, Semifinals |
| 12.01.2000 | | Bolton Wanderers | – | Tranmere Rovers | | 0:1 (0:1) |
| Bolton |
Football League Cup 1998/99, Fourth Round |
| 10.11.1998 | | Bolton Wanderers | – | Wimbledon | | 1:2 (0:1) |
| Bolton |
Football League Cup 1997/98, Fourth Round |
| 18.11.1997 | | Middlesbrough | – | Bolton Wanderers | | 2:1 aet
(1:1, 1:1) |
| Middlesbrough |
Football League Cup 1996/97, Fifth Round |
| 08.01.1997 | | Bolton Wanderers | – | Wimbledon | | 0:2 (0:2) |
| Bolton |
Football League Cup 1994/95, Final |
| 02.04.1995 | | Liverpool | – | Bolton Wanderers | | 2:1 (1:0) |
| London |
Football League Cup 1994/95, Semifinals |
| 12.02.1995 | | Swindon Town | – | Bolton Wanderers | | 2:1 (1:1) |
| Swindon |
Football League Cup 1993/94, Second round |
| 06.10.1993 | | Sheffield Wednesday | – | Bolton Wanderers | | 1:0 (0:0) |
| Sheffield |
Football League Cup 1993/94, First Round |
| 17.08.1993 | | Bolton Wanderers | – | Bury | | 0:2 (0:2) |
| Bolton |
Football League Cup 1992/93, Second round |
| 22.09.1992 | | Bolton Wanderers | – | Wimbledon | | 1:3 (0:2) |
| Bolton |
Football League Cup 1991/92, Second round |
| 08.10.1991 | | Bolton Wanderers | – | Nottingham Forest | | 2:5 (2:3) |
| Bolton |
Football League Cup 1991/92, Second round |
| 25.09.1991 | | Nottingham Forest | – | Bolton Wanderers | | 4:0 (2:0) |
| Nottingham |
Football League Cup 1990/91, Second round |
| 09.10.1990 | | Bolton Wanderers | – | Coventry City | | 2:3 |
| Bolton |
Football League Cup 1990/91, Second round |
| 26.09.1990 | | Coventry City | – | Bolton Wanderers | | 4:2 |
| Coventry |
Football League Cup 1989/90, Third round |
| 21.11.1989 | | Swindon Town | – | Bolton Wanderers | | 2:1 aet * |
| Swindon |
Football League Cup 1989/90, First Round |
| 22.08.1989 | | Rochdale | – | Bolton Wanderers | | 2:1 |
| Rochdale |
Football League Cup 1988/89, First Round |
| 07.09.1988 | | Chester City | – | Bolton Wanderers | | 3:1 |
| Chester |
Football League Cup 1987/88, First Round |
| 25.08.1987 | | Bolton Wanderers | – | Wigan Athletic | | 1:3 |
| Bolton |
Football League Cup 1986/87, First Round |
| 26.08.1986 | | Bury | – | Bolton Wanderers | | 2:1 |
| Bury |
Football League Cup 1985/86, Second round |
| 08.10.1985 | | Bolton Wanderers | – | Nottingham Forest | | 0:3 |
| |
Football League Cup 1985/86, Second round |
| 25.09.1985 | | Nottingham Forest | – | Bolton Wanderers | | 4:0 |
| |
Football League Cup 1984/85, Third round |
| 30.10.1984 | | Notts County | – | Bolton Wanderers | | 6:1 |
| |
Football League Cup 1983/84, First Round |
| 14.09.1983 | | Chester City | – | Bolton Wanderers | | 3:0 aet,
pen. 2:0 |
| |
Football League Cup 1982/83, Second round |
| 26.10.1982 | | Watford | – | Bolton Wanderers | | 2:1 aet |
| |
Football League Cup 1982/83, Second round |
| 05.10.1982 | | Bolton Wanderers | – | Watford | | 1:2 |
| |
Football League Cup 1981/82, First Round |
| 15.09.1981 | | Oldham Athletic | – | Bolton Wanderers | | 4:2 aet |
| |
Football League Cup 1980/81, Second round |
| 02.09.1980 | | Crystal Palace | – | Bolton Wanderers | | 2:1 |
| |
Football League Cup 1980/81, Second round |
| 26.08.1980 | | Bolton Wanderers | – | Crystal Palace | | 0:3 |
| |
Football League Cup 1979/80, Second round |
| 28.08.1979 | | Bolton Wanderers | – | Southend United | | 1:2 |
| |
Football League Cup 1978/79, Third round |
| 04.10.1978 | | Exeter City | – | Bolton Wanderers | | 2:1 |
| |
Football League Cup 1977/78, Fourth Round |
| 30.11.1977 | | Bolton Wanderers | – | Leeds United | | 1:3 |
| |
Football League Cup 1976/77, Semifinals |
| 15.02.1977 | | Bolton Wanderers | – | Everton | | 0:1 |
| Bolton |
Football League Cup 1975/76, Second round |
| 10.09.1975 | | Bolton Wanderers | – | Coventry City | | 1:3 |
| |
Football League Cup 1974/75, Second round |
| 17.09.1974 | | Norwich City | – | Bolton Wanderers | | 3:1 * |
| |
Football League Cup 1973/74, Third round |
| 06.11.1973 | | Bolton Wanderers | – | Millwall | | 1:2 * |
| |
Football League Cup 1972/73, Second round |
| 06.09.1972 | | Sheffield Wednesday | – | Bolton Wanderers | | 2:0 |
| |
Football League Cup 1971/72, Fourth Round |
| 08.11.1971 | | Bolton Wanderers | – | Chelsea | | 0:6 * |
| Bolton |
Football League Cup 1970/71, Third round |
| 12.10.1970 | | Leicester City | – | Bolton Wanderers | | 1:0 * |
| |
Football League Cup 1969/70, Second round |
| 11.09.1969 | | Rotherham United | – | Bolton Wanderers | | 1:0 * |
| |
Football League Cup 1968/69, Second round |
| 04.09.1968 | | West Ham United | – | Bolton Wanderers | | 7:2 |
| London |
Football League Cup 1967/68, Third round |
| 11.10.1967 | | West Ham United | – | Bolton Wanderers | | 4:1 |
| London |
Football League Cup 1966/67, Second round |
| 14.09.1966 | | Manchester City | – | Bolton Wanderers | | 3:1 |
| Manchester |
Football League Cup 1965/66, Third round |
| 13.10.1965 | | Grimsby Town | – | Bolton Wanderers | | 4:2 |
| |
Football League Cup 1964/65, Second round |
| 23.09.1964 | | Bolton Wanderers | – | Blackburn Rovers | | 1:5 |
| |
Football League Cup 1963/64, Third round |
| 29.10.1963 | | Stoke City | – | Bolton Wanderers | | 3:0 |
| |
Football League Cup 1962/63, Second round |
| 26.09.1962 | | Norwich City | – | Bolton Wanderers | | 4:0 |
| |
Football League Cup 1961/62, First Round |
| 25.09.1961 | | Sunderland | – | Bolton Wanderers | | 1:0 * |
| Sunderland |
Football League Cup 1960/61, Fourth Round |
| 20.12.1960 | | Bolton Wanderers | – | Rotherham United | | 0:2 |
| |
