Football League Cup 2023/24, Semifinals |
 | 23.01.2024 |  | Chelsea | – | Middlesbrough | | 6:1 (4:0) |
| London |
Football League Cup 2022/23, First Round |
| 10.08.2022 | | Middlesbrough | – | Barnsley | | 0:1 (0:0) |
| Middlesbrough |
Football League Cup 2021/22, First Round |
| 11.08.2021 | | Blackpool | – | Middlesbrough | | 3:0 (1:0) |
| Blackpool |
Football League Cup 2020/21, Second round |
| 15.09.2020 | | Middlesbrough | – | Barnsley | | 0:2 (0:2) * |
| Middlesbrough |
Football League Cup 2018/19, Fifth Round |
| 18.12.2018 | | Middlesbrough | – | Burton Albion | | 0:1 (0:0) |
| Middlesbrough |
Football League Cup 2017/18, Fourth Round |
| 24.10.2017 | | AFC Bournemouth | – | Middlesbrough | | 3:1 (0:0) |
| Bournemouth |
Football League Cup 2016/17, Second round |
| 24.08.2016 | | Fulham | – | Middlesbrough | | 2:1 aet
(0:1, 1:1) |
| London |
Football League Cup 2015/16, Fifth Round |
| 01.12.2015 | | Middlesbrough | – | Everton | | 0:2 (0:2) |
| Middlesbrough |
Football League Cup 2013/14, First Round |
| 06.08.2013 | | Middlesbrough | – | Accrington Stanley | | 1:2 (1:1) |
| Middlesbrough |
Football League Cup 2012/13, Fifth Round |
| 12.12.2012 |  | Swansea City | – | Middlesbrough | | 1:0 (0:0) |
| Swansea |
Football League Cup 2011/12, Third round |
| 20.09.2011 | | Crystal Palace | – | Middlesbrough | | 2:1 (1:0) |
| London |
Football League Cup 2010/11, Second round |
| 24.08.2010 | | Millwall | – | Middlesbrough | | 2:1 (2:0) |
| London |
Football League Cup 2009/10, Second round |
| 25.08.2009 | | Nottingham Forest | – | Middlesbrough | | 2:1 aet
(1:0, 1:1) |
| Nottingham |
Football League Cup 2008/09, Third round |
| 23.09.2008 | | Manchester United | – | Middlesbrough | | 3:1 (1:0) |
| Manchester |
Football League Cup 2007/08, Third round |
| 26.09.2007 | | Tottenham Hotspur | – | Middlesbrough | | 2:0 (0:0) |
| London |
Football League Cup 2006/07, Second round |
| 20.09.2006 | | Middlesbrough | – | Notts County | | 0:1 (0:1) |
| Middlesbrough |
Football League Cup 2005/06, Fifth Round |
| 21.12.2005 | | Middlesbrough | – | Blackburn Rovers | | 0:1 (0:0) |
| Middlesbrough |
Football League Cup 2004/05, Fourth Round |
| 10.11.2004 | | Liverpool | – | Middlesbrough | | 2:0 (0:0) |
| Liverpool |
Football League Cup 2002/03, Third round |
| 06.11.2002 | | Ipswich Town | – | Middlesbrough | | 3:1 (3:0) |
| Ipswich |
Football League Cup 2001/02, Third round |
| 10.10.2001 | | Blackburn Rovers | – | Middlesbrough | | 2:1 aet
(1:1, 1:1) |
| Blackburn |
Football League Cup 2000/01, Third round |
| 31.10.2000 | | Wimbledon | – | Middlesbrough | | 1:0 (0:0) |
| London |
Football League Cup 1999/00, Fifth Round |
| 14.12.1999 | | Tranmere Rovers | – | Middlesbrough | | 2:1 (1:0) |
| Birkenhead |
Football League Cup 1998/99, Third round |
| 28.10.1998 | | Middlesbrough | – | Everton | | 2:3 aet
(0:0, 1:1) |
| Middlesbrough |
Football League Cup 1997/98, Final |
| 29.03.1998 | | Chelsea | – | Middlesbrough | | 2:0 aet
(0:0) |
| London |
Football League Cup 1997/98, Semifinals |
| 27.01.1998 | | Liverpool | – | Middlesbrough | | 2:1 (1:1) |
| Liverpool |
Football League Cup 1996/97, Final |
| 16.04.1997 | | Leicester City | – | Middlesbrough | | 1:0 aet
(0:0) * |
| Sheffield |
Football League Cup 1996/97, Semifinals |
| 12.03.1997 | | Middlesbrough | – | Stockport County | | 0:1 (0:1) |
| Middlesbrough |
Football League Cup 1995/96, Fourth Round |
| 20.12.1995 | | Birmingham City | – | Middlesbrough | | 2:0 (2:0) * |
| Birmingham |
Football League Cup 1994/95, Third round |
| 26.10.1994 | | Aston Villa | – | Middlesbrough | | 1:0 (1:0) |
| Birmingham |
Football League Cup 1993/94, Third round |
| 10.11.1993 | | Sheffield Wednesday | – | Middlesbrough | | 2:1 (1:1) * |
| Sheffield |
Football League Cup 1992/93, Second round |
| 07.10.1992 | | Middlesbrough | – | Newcastle United | | 1:3 (0:1) |
| Middlesbrough |
Football League Cup 1991/92, Semifinals |
| 11.03.1992 | | Manchester United | – | Middlesbrough | | 2:1 aet |
| Manchester |
Football League Cup 1990/91, Fourth Round |
| 28.11.1990 | | Aston Villa | – | Middlesbrough | | 3:2 (1:0) |
| Birmingham |
Football League Cup 1990/91, Second round |
| 10.10.1990 | | Newcastle United | – | Middlesbrough | | 1:0 |
| Newcastle upon Tyne |
Football League Cup 1989/90, Third round |
| 08.11.1989 | | Wimbledon | – | Middlesbrough | | 1:0 * |
| London |
Football League Cup 1988/89, Second round |
| 11.10.1988 | | Tranmere Rovers | – | Middlesbrough | | 1:0 |
| Birkenhead |
Football League Cup 1987/88, Second round |
| 07.10.1987 | | Aston Villa | – | Middlesbrough | | 1:0 (1:0) |
| Birmingham |
Football League Cup 1987/88, Second round |
| 23.09.1987 | | Middlesbrough | – | Aston Villa | | 0:1 (0:1) |
| Middlesbrough |
Football League Cup 1987/88, First Round |
| 18.08.1987 | | Sunderland | – | Middlesbrough | | 1:0 |
| Sunderland |
Football League Cup 1986/87, Second round |
| 07.10.1986 | | Birmingham City | – | Middlesbrough | | 3:2 aet |
| Birmingham |
Football League Cup 1985/86, First Round |
| 21.08.1985 | | Mansfield Town | – | Middlesbrough | | 2:0 |
| |
Football League Cup 1984/85, First Round |
| 29.08.1984 | | Bradford City | – | Middlesbrough | | 2:0 |
| |
Football League Cup 1983/84, First Round |
| 30.08.1983 | | Middlesbrough | – | Chesterfield | | 0:1 |
| |
Football League Cup 1982/83, Second round |
| 05.10.1982 | | Burnley | – | Middlesbrough | | 3:2 |
| |
Football League Cup 1981/82, Third round |
| 10.11.1981 | | Liverpool | – | Middlesbrough | | 4:1 |
| Liverpool |
Football League Cup 1980/81, Second round |
| 02.09.1980 | | Ipswich Town | – | Middlesbrough | | 3:0 |
| |
Football League Cup 1979/80, Third round |
| 25.09.1979 | | Middlesbrough | – | Nottingham Forest | | 1:3 |
| |
Football League Cup 1978/79, Second round |
| 05.09.1978 | | Peterborough United | – | Middlesbrough | | 1:0 aet * |
| |
Football League Cup 1977/78, Third round |
| 31.10.1977 | | Middlesbrough | – | Everton | | 1:2 * |
| Middlesbrough |
Football League Cup 1976/77, Second round |
| 31.08.1976 | | Middlesbrough | – | Tottenham Hotspur | | 1:2 |
| Middlesbrough |
Football League Cup 1975/76, Semifinals |
| 21.01.1976 | | Manchester City | – | Middlesbrough | | 4:0 |
| Manchester |
Football League Cup 1974/75, Fifth Round |
| 18.12.1974 | | Manchester United | – | Middlesbrough | | 3:0 * |
| Manchester |
Football League Cup 1973/74, Third round |
| 06.11.1973 | | Middlesbrough | – | Stoke City | | 1:2 aet * |
| |
Football League Cup 1972/73, Third round |
| 30.10.1972 | | Tottenham Hotspur | – | Middlesbrough | | 2:1 aet * |
| London |
Football League Cup 1971/72, Second round |
| 14.09.1971 | | Middlesbrough | – | York City | | 1:2 * |
| |
Football League Cup 1970/71, Third round |
| 07.10.1970 | | Chelsea | – | Middlesbrough | | 3:2 |
| London |
Football League Cup 1969/70, Second round |
| 03.09.1969 | | Manchester United | – | Middlesbrough | | 1:0 |
| Manchester |
Football League Cup 1968/69, Second round |
| 04.09.1968 | | Bristol City | – | Middlesbrough | | 1:0 |
| |
Football League Cup 1967/68, Third round |
| 11.10.1967 | | Blackburn Rovers | – | Middlesbrough | | 3:2 |
| |
Football League Cup 1966/67, First Round |
| 29.08.1966 | | York City | – | Middlesbrough | | 2:1 * |
| |
Football League Cup 1965/66, Third round |
| 18.10.1965 | | Millwall | – | Middlesbrough | | 3:1 aet * |
| |
Football League Cup 1964/65, Second round |
| 23.09.1964 | | Charlton Athletic | – | Middlesbrough | | 2:1 |
| |
Football League Cup 1963/64, Second round |
| 02.10.1963 | | Middlesbrough | – | Bradford Park Avenue | | 2:3 * |
| |
Football League Cup 1962/63, Second round |
| 10.10.1962 | | Hull City | – | Middlesbrough | | 3:0 aet * |
| |
Football League Cup 1961/62, Third round |
| 15.11.1961 | | Norwich City | – | Middlesbrough | | 3:2 |
| |
Football League Cup 1960/61, First Round |
| 03.10.1960 | | Middlesbrough | – | Cardiff City | | 3:4 |
| |
