FA Cup 2021/22, Fourth Round Proper |
 | 04.02.2022 | | Manchester United | – | Middlesbrough | | 1:1 aet
(1:0, 1:1),
pen. 7:8 |
| Manchester |
FA Cup 2019/20, Third Round Proper |
| 05.01.2020 | | Middlesbrough | – | Tottenham Hotspur | | 1:1 (0:0) |
| Middlesbrough |
FA Cup 2018/19, Fourth Round Proper |
| 26.01.2019 | | Middlesbrough | – | Newport County | | 1:1 (0:0) |
| Middlesbrough |
FA Cup 2011/12, Fourth Round Proper |
| 29.01.2012 | | Sunderland | – | Middlesbrough | | 1:1 (0:1) |
| Sunderland |
FA Cup 2008/09, Fifth Round Proper |
| 14.02.2009 | | West Ham United | – | Middlesbrough | | 1:1 (0:1) |
| London |
FA Cup 2007/08, Fifth Round Proper |
| 17.02.2008 | | Sheffield United | – | Middlesbrough | | 0:0 |
| Sheffield |
FA Cup 2006/07, Sixth Round Proper |
| 10.03.2007 | | Middlesbrough | – | Manchester United | | 2:2 (1:1) |
| Middlesbrough |
FA Cup 2006/07, Fifth Round Proper |
| 27.02.2007 | | West Bromwich Albion | – | Middlesbrough | | 1:1 aet
(1:0, 1:1),
pen. 4:5 * |
| West Bromwich |
FA Cup 2006/07, Fifth Round Proper |
| 17.02.2007 | | Middlesbrough | – | West Bromwich Albion | | 2:2 (2:1) |
| Middlesbrough |
FA Cup 2006/07, Fourth Round Proper |
| 13.02.2007 | | Middlesbrough | – | Bristol City | | 2:2 aet
(0:1, 1:1),
pen. 5:4 * |
| Middlesbrough |
FA Cup 2006/07, Fourth Round Proper |
| 27.01.2007 | | Bristol City | – | Middlesbrough | | 2:2 aet
(0:2, 2:2),
pen. 4:5 |
| Bristol |
FA Cup 2006/07, Third Round Proper |
| 06.01.2007 | | Hull City | – | Middlesbrough | | 1:1 (0:0) |
| Kingston upon Hull |
FA Cup 2005/06, Sixth Round Proper |
| 23.03.2006 | | Charlton Athletic | – | Middlesbrough | | 0:0 |
| London |
FA Cup 2005/06, Fourth Round Proper |
| 28.01.2006 | | Coventry City | – | Middlesbrough | | 1:1 (0:0) |
| Coventry |
FA Cup 2005/06, Third Round Proper |
| 07.01.2006 | | Nuneaton Borough | – | Middlesbrough | | 1:1 (0:1) |
| Nuneaton Manor Park |
FA Cup 2001/02, Third Round Proper |
| 08.01.2002 | | Wimbledon | – | Middlesbrough | | 0:0 |
| London |
FA Cup 2000/01, Fourth Round Proper |
| 06.02.2001 | | Middlesbrough | – | Wimbledon | | 0:0 |
| Middlesbrough |
FA Cup 1997/98, Third Round Proper |
| 03.01.1998 | | Queens Park Rangers | – | Middlesbrough | | 2:2 (1:1) |
| London |
FA Cup 1996/97, Semi Final |
| 13.04.1997 | | Middlesbrough | – | Chesterfield | | 3:3 aet
(0:0, 2:2) |
| Manchester |
FA Cup 1995/96, Fourth Round Proper |
| 07.02.1996 | | Middlesbrough | – | Wimbledon | | 0:0 |
| Middlesbrough |
FA Cup 1994/95, Third Round Proper |
| 07.01.1995 | | Swansea City | – | Middlesbrough | | 1:1 (1:0) |
| Swansea |
FA Cup 1993/94, Third Round Proper |
| 08.01.1994 | | Cardiff City | – | Middlesbrough | | 2:2 (0:1) |
| Cardiff |
FA Cup 1992/93, Fourth Round Proper |
| 23.01.1993 | | Nottingham Forest | – | Middlesbrough | | 1:1 (0:1) |
| Nottingham |
FA Cup 1991/92, Fifth Round Proper |
| 15.02.1992 | | Portsmouth | – | Middlesbrough | | 1:1 |
| Portsmouth |
FA Cup 1990/91, Third Round Proper |
| 05.01.1991 | | Middlesbrough | – | Plymouth Argyle | | 0:0 |
| Middlesbrough |
FA Cup 1989/90, Third Round Proper |
| 10.01.1990 | | Everton | – | Middlesbrough | | 1:1 aet
(1:1) * |
| Liverpool |
FA Cup 1989/90, Third Round Proper |
| 06.01.1990 | | Middlesbrough | – | Everton | | 0:0 |
| Middlesbrough |
FA Cup 1987/88, Fourth Round Proper |
| 03.02.1988 | | Middlesbrough | – | Everton | | 2:2 aet
(0:0, 1:1) * |
| Middlesbrough |
FA Cup 1987/88, Fourth Round Proper |
| 30.01.1988 | | Everton | – | Middlesbrough | | 1:1 (1:0) |
| Liverpool |
FA Cup 1987/88, Third Round Proper |
| 09.01.1988 | | Sutton United | – | Middlesbrough | | 1:1 (0:0) |
| Sutton |
FA Cup 1984/85, Third Round Proper |
| 05.01.1985 | | Middlesbrough | – | Darlington | | 0:0 |
| |
FA Cup 1982/83, Fifth Round Proper |
| 19.02.1983 | | Middlesbrough | – | Arsenal | | 1:1 |
| |
FA Cup 1982/83, Third Round Proper |
| 08.01.1983 | | Middlesbrough | – | Bishop's Stortford | | 2:2 |
| |
FA Cup 1981/82, Third Round Proper |
| 02.01.1982 | | Queens Park Rangers | – | Middlesbrough | | 1:1 |
| |
FA Cup 1980/81, Sixth Round Proper |
| 07.03.1981 | | Middlesbrough | – | Wolverhampton Wanderers | | 1:1 |
| |
FA Cup 1979/80, Third Round Proper |
| 09.01.1980 | | Portsmouth | – | Middlesbrough | | 1:1 |
| |
FA Cup 1978/79, Third Round Proper |
| 09.01.1979 | | Middlesbrough | – | Crystal Palace | | 1:1 |
| |
FA Cup 1977/78, Sixth Round Proper |
| 11.03.1978 | | Middlesbrough | – | Orient | | 0:0 |
| |
FA Cup 1976/77, Third Round Proper |
| 08.01.1977 | | Wimbledon | – | Middlesbrough | | 0:0 |
| |
FA Cup 1975/76, Third Round Proper |
| 03.01.1976 | | Middlesbrough | – | Bury | | 0:0 |
| |
FA Cup 1974/75, Fifth Round Proper |
| 15.02.1975 | | Peterborough United | – | Middlesbrough | | 1:1 |
| |
FA Cup 1974/75, Third Round Proper |
| 04.01.1975 | | Wycombe Wanderers | – | Middlesbrough | | 0:0 |
| |
FA Cup 1971/72, Fifth Round Proper |
| 26.02.1972 | | Manchester United | – | Middlesbrough | | 0:0 |
| |
FA Cup 1971/72, Fourth Round Proper |
| 05.02.1972 | | Millwall | – | Middlesbrough | | 2:2 |
| |
FA Cup 1971/72, Third Round Proper |
| 15.01.1972 | | Manchester City | – | Middlesbrough | | 1:1 |
| |
FA Cup 1970/71, Third Round Proper |
| 02.01.1971 | | Manchester United | – | Middlesbrough | | 0:0 |
| |
FA Cup 1969/70, Sixth Round Proper |
| 21.02.1970 | | Middlesbrough | – | Manchester United | | 1:1 (1:1) |
| |
FA Cup 1968/69, Third Round Proper |
| 04.01.1969 | | Middlesbrough | – | Millwall | | 1:1 |
| |
FA Cup 1967/68, Fourth Round Proper |
| 17.02.1968 | | Middlesbrough | – | Bristol City | | 1:1 |
| |
FA Cup 1967/68, Third Round Proper |
| 31.01.1968 | | Hull City | – | Middlesbrough | | 2:2 aet * |
| |
FA Cup 1967/68, Third Round Proper |
| 27.01.1968 | | Middlesbrough | – | Hull City | | 1:1 |
| |
FA Cup 1966/67, Second Round Proper |
| 11.01.1967 | | York City | – | Middlesbrough | | 0:0 aet * |
| |
FA Cup 1966/67, Second Round Proper |
| 07.01.1967 | | Middlesbrough | – | York City | | 1:1 |
| |
FA Cup 1964/65, Fourth Round Proper |
| 30.01.1965 | | Charlton Athletic | – | Middlesbrough | | 1:1 |
| |
FA Cup 1962/63, Third Round Proper |
| 05.03.1963 | | Blackburn Rovers | – | Middlesbrough | | 1:1 |
| |
FA Cup 1961/62, Fourth Round Proper |
| 27.01.1962 | | Shrewsbury Town | – | Middlesbrough | | 2:2 |
| |
FA Cup 1956/57, Third Round Proper |
| 05.01.1957 | | Middlesbrough | – | Charlton Athletic | | 1:1 |
| |
FA Cup 1953/54, Third Round Proper |
| 09.01.1954 | | Middlesbrough | – | Leicester City | | 0:0 |
| |
FA Cup 1951/52, Third Round Proper |
| 12.01.1952 | | Middlesbrough | – | Derby County | | 2:2 |
| |
FA Cup 1949/50, Third Round Proper |
| 11.01.1950 | | Middlesbrough | – | Aston Villa | | 0:0 aet * |
| |
FA Cup 1949/50, Third Round Proper |
| 07.01.1950 | | Aston Villa | – | Middlesbrough | | 2:2 |
| |
FA Cup 1946/47, Sixth Round Proper |
| 01.03.1947 | | Middlesbrough | – | Burnley | | 1:1 |
| |
FA Cup 1946/47, Fifth Round Proper |
| 08.02.1947 | | Nottingham Forest | – | Middlesbrough | | 2:2 |
| |
FA Cup 1946/47, Third Round Proper |
| 11.01.1947 | | Queens Park Rangers | – | Middlesbrough | | 1:1 |
| |
FA Cup 1945/46, Fifth Round Proper |
| 13.02.1946 | | Middlesbrough | – | Bolton Wanderers | | 1:1 |
| |
FA Cup 1945/46, Third Round Proper |
| 05.01.1946 | | Leeds United | – | Middlesbrough | | 4:4 |
| |
FA Cup 1938/39, Third Round Proper |
| 11.01.1939 | | Bolton Wanderers | – | Middlesbrough | | 0:0 aet * |
| |
FA Cup 1938/39, Third Round Proper |
| 07.01.1939 | | Middlesbrough | – | Bolton Wanderers | | 0:0 |
| |
FA Cup 1934/35, Third Round Proper |
| 12.01.1935 | | Middlesbrough | – | Blackburn Rovers | | 1:1 |
| |
FA Cup 1933/34, Third Round Proper |
| 13.01.1934 | | Sunderland | – | Middlesbrough | | 1:1 |
| |
FA Cup 1932/33, Fifth Round Proper |
| 18.02.1933 | | Middlesbrough | – | Birmingham | | 0:0 |
| |
FA Cup 1931/32, Third Round Proper |
| 09.01.1932 | | Middlesbrough | – | Portsmouth | | 1:1 |
| |
FA Cup 1930/31, Third Round Proper |
| 14.01.1931 | | Middlesbrough | – | Bradford City | | 1:1 |
| |
FA Cup 1929/30, Fourth Round Proper |
| 29.01.1930 | | Charlton Athletic | – | Middlesbrough | | 1:1 aet * |
| |
FA Cup 1929/30, Fourth Round Proper |
| 25.01.1930 | | Middlesbrough | – | Charlton Athletic | | 1:1 |
| |
FA Cup 1929/30, Third Round Proper |
| 11.01.1930 | | Chesterfield | – | Middlesbrough | | 1:1 |
| |
FA Cup 1928/29, Third Round Proper |
| 12.01.1929 | | Walsall | – | Middlesbrough | | 1:1 |
| |
FA Cup 1922/23, Second Round Proper |
| 03.02.1923 | | Middlesbrough | – | Sheffield United | | 1:1 |
| |
FA Cup 1912/13, First Round Proper |
| 11.01.1913 | | Millwall | – | Middlesbrough | | 0:0 |
| |
FA Cup 1911/12, Second Round Proper |
| 03.02.1912 | | Middlesbrough | – | West Ham United | | 1:1 |
| |
FA Cup 1911/12, First Round Proper |
| 13.01.1912 | | Middlesbrough | – | Sheffield Wednesday | | 0:0 |
| |
FA Cup 1910/11, Second Round Proper |
| 04.02.1911 | | Middlesbrough | – | Leicester Fosse | | 0:0 |
| |
FA Cup 1909/10, First Round Proper |
| 15.01.1910 | | Middlesbrough | – | Everton | | 1:1 |
| |
FA Cup 1905/06, Second Round Proper |
| 07.02.1906 | | Middlesbrough | – | Brighton & Hove Albion | | 1:1 aet * |
| |
FA Cup 1905/06, Second Round Proper |
| 03.02.1906 | | Brighton & Hove Albion | – | Middlesbrough | | 1:1 |
| |
FA Cup 1904/05, First Round Proper |
| 04.02.1905 | | Middlesbrough | – | Tottenham Hotspur | | 1:1 |
| |
FA Cup 1903/04, Third Round Proper |
| 05.03.1904 | | Manchester City | – | Middlesbrough | | 0:0 |
| |
FA Cup 1901/02, First Round Proper |
| 25.01.1902 | | Middlesbrough | – | Bristol Rovers | | 1:1 |
| |
FA Cup 1887/88, Third Round |
| 26.11.1887 | | Middlesbrough | – | Sunderland | | 2:2 |
| |
FA Cup 1886/87, Second Round |
| 20.11.1886 | | Middlesbrough | – | Lincoln City | | 1:1 |
| |
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