Football League Cup 2023/24, Semifinals |
 | 09.01.2024 |  | Middlesbrough | – | Chelsea | | 1:0 (1:0) |
| Middlesbrough |
Football League Cup 2023/24, Fifth Round |
| 19.12.2023 | | Port Vale | – | Middlesbrough | | 0:3 (0:2) |
| Stoke-on-Trent |
Football League Cup 2023/24, Fourth Round |
| 31.10.2023 | | Exeter City | – | Middlesbrough | | 2:3 (1:0) |
| Exeter |
Football League Cup 2023/24, Third Round |
| 26.09.2023 | | Bradford City | – | Middlesbrough | | 0:2 (0:1) |
| Bradford |
Football League Cup 2023/24, Second Round |
| 29.08.2023 | | Bolton Wanderers | – | Middlesbrough | | 1:3 (1:1) |
| Bolton |
Football League Cup 2023/24, First Round |
| 08.08.2023 | | Huddersfield Town | – | Middlesbrough | | 2:3 (1:1) |
| Huddersfield |
Football League Cup 2020/21, First Round |
| 04.09.2020 | | Middlesbrough | – | Shrewsbury Town | | 4:3 (2:1) * |
| Middlesbrough |
Football League Cup 2018/19, Fourth Round |
| 31.10.2018 | | Middlesbrough | – | Crystal Palace | | 1:0 (1:0) |
| Middlesbrough |
Football League Cup 2018/19, Second round |
| 28.08.2018 | | Middlesbrough | – | Rochdale | | 2:1 (1:0) |
| Middlesbrough |
Football League Cup 2017/18, Third round |
| 19.09.2017 | | Aston Villa | – | Middlesbrough | | 0:2 (0:0) |
| Birmingham |
Football League Cup 2017/18, Second round |
| 22.08.2017 | | Middlesbrough | – | Scunthorpe United | | 3:0 (2:0) |
| Middlesbrough |
Football League Cup 2015/16, Third round |
| 22.09.2015 | | Middlesbrough | – | Wolverhampton Wanderers | | 3:0 (1:0) |
| Middlesbrough |
Football League Cup 2015/16, Second round |
| 25.08.2015 | | Burton Albion | – | Middlesbrough | | 1:2 aet
(1:0, 1:1) |
| Burton upon Trent |
Football League Cup 2015/16, First Round |
| 12.08.2015 | | Oldham Athletic | – | Middlesbrough | | 1:3 (0:2) |
| Oldham |
Football League Cup 2014/15, Second round |
| 26.08.2014 | | Middlesbrough | – | Preston North End | | 3:1 (0:0) |
| Middlesbrough |
Football League Cup 2014/15, First Round |
| 12.08.2014 | | Oldham Athletic | – | Middlesbrough | | 0:3 (0:1) |
| Oldham |
Football League Cup 2012/13, Fourth Round |
| 30.10.2012 | | Sunderland | – | Middlesbrough | | 0:1 (0:1) |
| Sunderland |
Football League Cup 2012/13, Third round |
| 25.09.2012 | | Preston North End | – | Middlesbrough | | 1:3 (1:2) |
| Preston |
Football League Cup 2012/13, Second round |
| 28.08.2012 | | Gillingham | – | Middlesbrough | | 0:2 (0:1) |
| Gillingham |
Football League Cup 2012/13, First Round |
| 11.08.2012 | | Bury | – | Middlesbrough | | 1:2 (0:1) |
| Bury |
Football League Cup 2011/12, Second round |
| 24.08.2011 | | Peterborough United | – | Middlesbrough | | 0:2 (0:2) |
| Peterborough |
Football League Cup 2011/12, First Round |
| 09.08.2011 | | Walsall | – | Middlesbrough | | 0:3 (0:2) |
| Walsall |
Football League Cup 2010/11, First Round |
| 10.08.2010 | | Chesterfield | – | Middlesbrough | | 1:2 (0:2) |
| Chesterfield |
Football League Cup 2008/09, Second round |
| 26.08.2008 | | Middlesbrough | – | Yeovil Town | | 5:1 (3:1) |
| Middlesbrough |
Football League Cup 2007/08, Second round |
| 29.08.2007 | | Middlesbrough | – | Northampton Town | | 2:0 (0:0) |
| Middlesbrough |
Football League Cup 2005/06, Fourth Round |
| 30.11.2005 | | Middlesbrough | – | Crystal Palace | | 2:1 (0:1) |
| Middlesbrough |
Football League Cup 2005/06, Third round |
| 26.10.2005 | | Everton | – | Middlesbrough | | 0:1 (0:1) |
| Liverpool |
Football League Cup 2004/05, Third round |
| 27.10.2004 | | Middlesbrough | – | Coventry City | | 3:0 (2:0) |
| Middlesbrough |
Football League Cup 2003/04, Final |
| 29.02.2004 | | Bolton Wanderers | – | Middlesbrough | | 1:2 (1:2) |
| Cardiff |
Football League Cup 2003/04, Semifinals |
| 03.02.2004 | | Middlesbrough | – | Arsenal | | 2:1 (0:0) |
| Middlesbrough |
Football League Cup 2003/04, Semifinals |
| 20.01.2004 | | Arsenal | – | Middlesbrough | | 0:1 (0:0) |
| London |
Football League Cup 2003/04, Third round |
| 29.10.2003 | | Wigan Athletic | – | Middlesbrough | | 1:2 (0:1) |
| Wigan |
Football League Cup 2003/04, Second round |
| 24.09.2003 | | Middlesbrough | – | Brighton & Hove Albion | | 1:0 aet
(0:0) |
| Middlesbrough |
Football League Cup 2002/03, Second round |
| 01.10.2002 | | Brentford | – | Middlesbrough | | 1:4 (0:2) |
| Brentford |
Football League Cup 2001/02, Second round |
| 11.09.2001 | | Middlesbrough | – | Northampton Town | | 3:1 (0:0) |
| Middlesbrough |
Football League Cup 2000/01, Second round |
| 26.09.2000 | | Macclesfield Town | – | Middlesbrough | | 1:3 (1:1) |
| Macclesfield |
Football League Cup 2000/01, Second round |
| 19.09.2000 | | Middlesbrough | – | Macclesfield Town | | 2:1 (0:0) |
| Middlesbrough |
Football League Cup 1999/00, Third round |
| 13.10.1999 | | Middlesbrough | – | Watford | | 1:0 (0:0) |
| Middlesbrough |
Football League Cup 1999/00, Second round |
| 21.09.1999 | | Middlesbrough | – | Chesterfield | | 2:1 (1:0) |
| Middlesbrough |
Football League Cup 1998/99, Second round |
| 16.09.1998 | | Middlesbrough | – | Wycombe Wanderers | | 2:0 (1:0) |
| Middlesbrough |
Football League Cup 1997/98, Semifinals |
| 18.02.1998 | | Middlesbrough | – | Liverpool | | 2:0 (2:0) |
| Middlesbrough |
Football League Cup 1997/98, Fifth Round |
| 06.01.1998 | | Reading | – | Middlesbrough | | 0:1 (0:0) |
| Reading |
Football League Cup 1997/98, Fourth Round |
| 18.11.1997 | | Middlesbrough | – | Bolton Wanderers | | 2:1 aet
(1:1, 1:1) |
| Middlesbrough |
Football League Cup 1997/98, Third round |
| 15.10.1997 | | Middlesbrough | – | Sunderland | | 2:0 (0:0) |
| Middlesbrough |
Football League Cup 1997/98, Second round |
| 23.09.1997 | | Barnet | – | Middlesbrough | | 0:2 (0:1) |
| London |
Football League Cup 1997/98, Second round |
| 16.09.1997 | | Middlesbrough | – | Barnet | | 1:0 (0:0) |
| Middlesbrough |
Football League Cup 1996/97, Semifinals |
| 26.02.1997 | | Stockport County | – | Middlesbrough | | 0:2 (0:0) |
| Stockport |
Football League Cup 1996/97, Fifth Round |
| 08.01.1997 | | Middlesbrough | – | Liverpool | | 2:1 (2:0) |
| Middlesbrough |
Football League Cup 1996/97, Fourth Round |
| 27.11.1996 | | Middlesbrough | – | Newcastle United | | 3:1 (1:1) |
| Middlesbrough |
Football League Cup 1996/97, Third round |
| 23.10.1996 | | Middlesbrough | – | Huddersfield Town | | 5:1 (2:0) |
| Middlesbrough |
Football League Cup 1996/97, Second round |
| 24.09.1996 | | Hereford United | – | Middlesbrough | | 0:3 (0:1) |
| Hereford |
Football League Cup 1996/97, Second round |
| 18.09.1996 | | Middlesbrough | – | Hereford United | | 7:0 (3:0) |
| Middlesbrough |
Football League Cup 1995/96, Third round |
| 08.11.1995 | | Middlesbrough | – | Crystal Palace | | 2:0 (1:0) * |
| Middlesbrough |
Football League Cup 1995/96, Second round |
| 03.10.1995 | | Rotherham United | – | Middlesbrough | | 0:1 (0:0) |
| Rotherham |
Football League Cup 1995/96, Second round |
| 20.09.1995 | | Middlesbrough | – | Rotherham United | | 2:1 (2:1) |
| Middlesbrough |
Football League Cup 1994/95, Second round |
| 27.09.1994 | | Middlesbrough | – | Scarborough | | 4:1 (1:1) |
| Middlesbrough |
Football League Cup 1994/95, Second round |
| 20.09.1994 | | Scarborough | – | Middlesbrough | | 1:4 (1:4) |
| Scarborough |
Football League Cup 1993/94, Second round |
| 06.10.1993 | | Brighton & Hove Albion | – | Middlesbrough | | 1:3 (0:2) |
| Hove |
Football League Cup 1993/94, Second round |
| 21.09.1993 | | Middlesbrough | – | Brighton & Hove Albion | | 5:0 (4:0) |
| Middlesbrough |
Football League Cup 1991/92, Fifth Round |
| 12.02.1992 | | Middlesbrough | – | Peterborough United | | 1:0 (0:0) * |
| Middlesbrough |
Football League Cup 1991/92, Fourth Round |
| 03.12.1991 | | Middlesbrough | – | Manchester City | | 2:1 (0:0) |
| Middlesbrough |
Football League Cup 1991/92, Third round |
| 29.10.1991 | | Middlesbrough | – | Barnsley | | 1:0 (1:0) |
| Middlesbrough |
Football League Cup 1991/92, Second round |
| 08.10.1991 | | Bournemouth | – | Middlesbrough | | 1:2 aet |
| Bournemouth |
Football League Cup 1990/91, Third round |
| 30.10.1990 | | Middlesbrough | – | Norwich City | | 2:0 |
| Middlesbrough |
Football League Cup 1990/91, Second round |
| 25.09.1990 | | Middlesbrough | – | Newcastle United | | 2:0 |
| Middlesbrough |
Football League Cup 1990/91, First Round |
| 03.09.1990 | | Tranmere Rovers | – | Middlesbrough | | 1:2 |
| Birkenhead |
Football League Cup 1989/90, Second round |
| 03.10.1989 | | Halifax Town | – | Middlesbrough | | 0:1 |
| Halifax |
Football League Cup 1989/90, Second round |
| 20.09.1989 | | Middlesbrough | – | Halifax Town | | 4:0 |
| Middlesbrough |
Football League Cup 1987/88, First Round |
| 25.08.1987 | | Middlesbrough | – | Sunderland | | 2:0 |
| Middlesbrough |
Football League Cup 1986/87, First Round |
| 02.09.1986 | | Middlesbrough | – | Hartlepool United | | 2:0 |
| Middlesbrough |
Football League Cup 1983/84, First Round |
| 13.09.1983 | | Chesterfield | – | Middlesbrough | | 0:1 aet,
pen. 5:3 |
| |
Football League Cup 1981/82, Second round |
| 06.10.1981 | | Middlesbrough | – | Plymouth Argyle | | 2:1 |
| |
Football League Cup 1980/81, Second round |
| 26.08.1980 | | Middlesbrough | – | Ipswich Town | | 3:1 |
| |
Football League Cup 1979/80, Second round |
| 29.08.1979 | | Derby County | – | Middlesbrough | | 0:1 |
| |
Football League Cup 1977/78, Second round |
| 13.09.1977 | | Middlesbrough | – | Sunderland | | 1:0 * |
| |
Football League Cup 1975/76, Semifinals |
| 13.01.1976 | | Middlesbrough | – | Manchester City | | 1:0 |
| Middlesbrough |
Football League Cup 1975/76, Fifth Round |
| 03.12.1975 | | Burnley | – | Middlesbrough | | 0:2 |
| |
Football League Cup 1975/76, Fourth Round |
| 11.11.1975 | | Middlesbrough | – | Peterborough United | | 3:0 |
| |
Football League Cup 1975/76, Third round |
| 07.10.1975 | | Middlesbrough | – | Derby County | | 1:0 |
| |
Football League Cup 1975/76, Second round |
| 09.09.1975 | | Bury | – | Middlesbrough | | 1:2 |
| |
Football League Cup 1974/75, Fourth Round |
| 12.11.1974 | | Liverpool | – | Middlesbrough | | 0:1 |
| Liverpool |
Football League Cup 1974/75, Third round |
| 08.10.1974 | | Middlesbrough | – | Leicester City | | 1:0 |
| |
Football League Cup 1974/75, Second round |
| 11.09.1974 | | Tottenham Hotspur | – | Middlesbrough | | 0:4 |
| London |
Football League Cup 1973/74, Second round |
| 08.10.1973 | | Manchester United | – | Middlesbrough | | 0:1 |
| Manchester |
Football League Cup 1972/73, Second round |
| 05.09.1972 | | Middlesbrough | – | Wrexham |  | 2:0 |
| |
Football League Cup 1970/71, Second round |
| 08.09.1970 | | Oldham Athletic | – | Middlesbrough | | 2:4 |
| |
Football League Cup 1967/68, Second round |
| 13.09.1967 | | Middlesbrough | – | Chelsea | | 2:1 |
| Middlesbrough |
Football League Cup 1967/68, First Round |
| 22.08.1967 | | Middlesbrough | – | Barnsley | | 4:1 |
| |
Football League Cup 1965/66, Second round |
| 22.09.1965 | | Colchester United | – | Middlesbrough | | 2:4 |
| |
Football League Cup 1961/62, Second round |
| 04.10.1961 | | Middlesbrough | – | Crewe Alexandra | | 3:1 |
| |
Football League Cup 1961/62, First Round |
| 13.09.1961 | | Tranmere Rovers | – | Middlesbrough | | 3:6 |
| |
