Football League Cup 2019/20, First Round |
 | 13.08.2019 |  | Middlesbrough | – | Crewe Alexandra | | 2:2 (0:2),
pen. 2:4 |
| Middlesbrough |
Football League Cup 2018/19, Third round |
| 25.09.2018 | | Preston North End | – | Middlesbrough | | 2:2 (1:1),
pen. 3:4 |
| Preston |
Football League Cup 2018/19, First Round |
| 14.08.2018 | | Middlesbrough | – | Notts County | | 3:3 (2:2),
pen. 4:3 |
| Middlesbrough |
Football League Cup 2015/16, Fourth Round |
| 28.10.2015 | | Manchester United | – | Middlesbrough | | 0:0 aet,
pen. 1:3 |
| Manchester |
Football League Cup 2014/15, Third round |
| 23.09.2014 | | Liverpool | – | Middlesbrough | | 2:2 aet
(1:0, 1:1),
pen. 14:13 |
| Liverpool |
Football League Cup 2003/04, Fifth Round |
| 17.12.2003 | | Tottenham Hotspur | – | Middlesbrough | | 1:1 aet
(1:0, 1:1),
pen. 4:5 |
| London |
Football League Cup 2003/04, Fourth Round |
| 03.12.2003 | | Middlesbrough | – | Everton | | 0:0 aet,
pen. 5:4 |
| Middlesbrough |
Football League Cup 1999/00, Fourth Round |
| 30.11.1999 | | Middlesbrough | – | Arsenal | | 2:2 aet
(1:1, 2:2),
pen. 3:1 |
| Middlesbrough |
Football League Cup 1999/00, Second round |
| 14.09.1999 | | Chesterfield | – | Middlesbrough | | 0:0 |
| Chesterfield |
Football League Cup 1998/99, Second round |
| 22.09.1998 | | Wycombe Wanderers | – | Middlesbrough | | 1:1 (1:0) |
| High Wycombe |
Football League Cup 1996/97, Final |
| 06.04.1997 | | Leicester City | – | Middlesbrough | | 1:1 aet
(0:0) |
| London |
Football League Cup 1995/96, Fourth Round |
| 29.11.1995 | | Middlesbrough | – | Birmingham City | | 0:0 |
| Middlesbrough |
Football League Cup 1995/96, Third round |
| 25.10.1995 | | Crystal Palace | – | Middlesbrough | | 2:2 (2:2) |
| London |
Football League Cup 1993/94, Third round |
| 27.10.1993 | | Middlesbrough | – | Sheffield Wednesday | | 1:1 (0:0) |
| Middlesbrough |
Football League Cup 1992/93, Second round |
| 23.09.1992 | | Newcastle United | – | Middlesbrough | | 0:0 |
| Newcastle upon Tyne |
Football League Cup 1991/92, Semifinals |
| 04.03.1992 | | Middlesbrough | – | Manchester United | | 0:0 |
| Middlesbrough |
Football League Cup 1991/92, Fifth Round |
| 08.01.1992 | | Peterborough United | – | Middlesbrough | | 0:0 |
| Peterborough |
Football League Cup 1991/92, Second round |
| 24.09.1991 | | Middlesbrough | – | Bournemouth | | 1:1 (0:0) |
| Middlesbrough |
Football League Cup 1990/91, First Round |
| 28.08.1990 | | Middlesbrough | – | Tranmere Rovers | | 1:1 |
| Middlesbrough |
Football League Cup 1989/90, Third round |
| 25.10.1989 | | Middlesbrough | – | Wimbledon | | 1:1 |
| Middlesbrough |
Football League Cup 1988/89, Second round |
| 28.09.1988 | | Middlesbrough | – | Tranmere Rovers | | 0:0 |
| Middlesbrough |
Football League Cup 1986/87, Second round |
| 23.09.1986 | | Middlesbrough | – | Birmingham City | | 2:2 |
| Middlesbrough |
Football League Cup 1986/87, First Round |
| 26.08.1986 | | Hartlepool United | – | Middlesbrough | | 1:1 |
| Hartlepool |
Football League Cup 1985/86, First Round |
| 03.09.1985 | | Middlesbrough | – | Mansfield Town | | 4:4 |
| |
Football League Cup 1984/85, First Round |
| 04.09.1984 | | Middlesbrough | – | Bradford City | | 2:2 |
| |
Football League Cup 1982/83, Second round |
| 26.10.1982 | | Middlesbrough | – | Burnley | | 1:1 |
| |
Football League Cup 1981/82, Second round |
| 27.10.1981 | | Plymouth Argyle | – | Middlesbrough | | 0:0 |
| |
Football League Cup 1979/80, Second round |
| 04.09.1979 | | Middlesbrough | – | Derby County | | 1:1 aet |
| |
Football League Cup 1978/79, Second round |
| 29.08.1978 | | Middlesbrough | – | Peterborough United | | 0:0 |
| |
Football League Cup 1977/78, Third round |
| 25.10.1977 | | Everton | – | Middlesbrough | | 2:2 |
| Liverpool |
Football League Cup 1977/78, Second round |
| 30.08.1977 | | Sunderland | – | Middlesbrough | | 2:2 |
| Sunderland |
Football League Cup 1974/75, Fifth Round |
| 04.12.1974 | | Middlesbrough | – | Manchester United | | 0:0 |
| Middlesbrough |
Football League Cup 1973/74, Third round |
| 31.10.1973 | | Stoke City | – | Middlesbrough | | 1:1 |
| |
Football League Cup 1972/73, Third round |
| 11.10.1972 | | Tottenham Hotspur | – | Middlesbrough | | 0:0 aet * |
| London |
Football League Cup 1972/73, Third round |
| 03.10.1972 | | Middlesbrough | – | Tottenham Hotspur | | 1:1 |
| Middlesbrough |
Football League Cup 1971/72, Second round |
| 08.09.1971 | | York City | – | Middlesbrough | | 2:2 |
| |
Football League Cup 1966/67, First Round |
| 24.08.1966 | | Middlesbrough | – | York City | | 0:0 |
| |
Football League Cup 1965/66, Third round |
| 13.10.1965 | | Millwall | – | Middlesbrough | | 0:0 |
| |
Football League Cup 1963/64, Second round |
| 25.09.1963 | | Bradford Park Avenue | – | Middlesbrough | | 2:2 |
| |
Football League Cup 1962/63, Second round |
| 08.10.1962 | | Middlesbrough | – | Hull City | | 1:1 aet * |
| |
Football League Cup 1962/63, Second round |
| 24.09.1962 | | Hull City | – | Middlesbrough | | 2:2 |
| |
