FA Cup 2023/24, Third Round Proper |
| 06.01.2024 | | Middlesbrough | | Aston Villa | | 0:1 (0:0) |
| Middlesbrough |
FA Cup 2022/23, Third Round Proper |
| 07.01.2023 | | Middlesbrough | | Brighton & Hove Albion | | 1:5 (1:2) |
| Middlesbrough |
FA Cup 2021/22, Quarterfinal |
| 19.03.2022 | | Middlesbrough | | Chelsea | | 0:2 (0:2) |
| Middlesbrough |
FA Cup 2020/21, Third Round Proper |
| 09.01.2021 | | Brentford | | Middlesbrough | | 2:1 (1:0) * |
| Brentford |
FA Cup 2019/20, Third Round Proper |
| 14.01.2020 | | Tottenham Hotspur | | Middlesbrough | | 2:1 (2:0) * |
| London |
FA Cup 2018/19, Fourth Round Proper |
| 05.02.2019 | | Newport County | | Middlesbrough | | 2:0 (0:0) * |
| Newport |
FA Cup 2017/18, Fourth Round Proper |
| 27.01.2018 | | Middlesbrough | | Brighton & Hove Albion | | 0:1 (0:0) |
| Middlesbrough |
FA Cup 2016/17, Sixth round proper |
| 11.03.2017 | | Middlesbrough | | Manchester City | | 0:2 (0:1) |
| Middlesbrough |
FA Cup 2015/16, Third Round Proper |
| 09.01.2016 | | Middlesbrough | | Burnley | | 1:2 (1:1) |
| Middlesbrough |
FA Cup 2014/15, Fifth Round Proper |
| 15.02.2015 | | Arsenal | | Middlesbrough | | 2:0 (2:0) |
| London |
FA Cup 2013/14, Third Round Proper |
| 04.01.2014 | | Middlesbrough | | Hull City | | 0:2 (0:1) |
| Middlesbrough |
FA Cup 2012/13, Fifth Round Proper |
| 27.02.2013 | | Middlesbrough | | Chelsea | | 0:2 (0:0) |
| Middlesbrough |
FA Cup 2011/12, Fourth Round Proper |
| 08.02.2012 | | Middlesbrough | | Sunderland | | 1:2 aet (0:1, 1:1) * |
| Middlesbrough |
FA Cup 2010/11, Third Round Proper |
| 08.01.2011 | | Burton Albion | | Middlesbrough | | 2:1 (0:0) |
| Burton upon Trent |
FA Cup 2009/10, Third Round Proper |
| 02.01.2010 | | Middlesbrough | | Manchester City | | 0:1 (0:1) |
| Middlesbrough |
FA Cup 2008/09, Sixth Round Proper |
| 08.03.2009 | | Everton | | Middlesbrough | | 2:1 (0:1) |
| Liverpool |
FA Cup 2007/08, Sixth Round Proper |
| 09.03.2008 | | Middlesbrough | | Cardiff City | | 0:2 (0:2) |
| Middlesbrough |
FA Cup 2006/07, Sixth Round Proper |
| 19.03.2007 | | Manchester United | | Middlesbrough | | 1:0 (0:0) * |
| Manchester |
FA Cup 2005/06, Semi Final |
| 23.04.2006 | | Middlesbrough | | West Ham United | | 0:1 (0:0) |
| Birmingham |
FA Cup 2004/05, Fourth Round Proper |
| 29.01.2005 | | Manchester United | | Middlesbrough | | 3:0 (1:0) |
| Manchester |
FA Cup 2003/04, Fourth Round Proper |
| 24.01.2004 | | Arsenal | | Middlesbrough | | 4:1 (2:1) |
| London |
FA Cup 2002/03, Third Round Proper |
| 04.01.2003 | | Chelsea | | Middlesbrough | | 1:0 (1:0) |
| London |
FA Cup 2001/02, Semi Final |
| 14.04.2002 | | Arsenal | | Middlesbrough | | 1:0 (1:0) |
| Manchester |
FA Cup 2000/01, Fourth Round Proper |
| 13.02.2001 | | Wimbledon | | Middlesbrough | | 3:1 aet (0:1, 1:1) * |
| London |
FA Cup 1999/00, Third Round Proper |
| 11.12.1999 | | Wrexham | | Middlesbrough | | 2:1 (0:1) |
| Wrexham |
FA Cup 1998/99, Third Round Proper |
| 03.01.1999 | | Manchester United | | Middlesbrough | | 3:1 (0:0) |
| Manchester |
FA Cup 1997/98, Fourth Round Proper |
| 24.01.1998 | | Middlesbrough | | Arsenal | | 1:2 (0:2) |
| Middlesbrough |
FA Cup 1996/97, Final |
| 17.05.1997 | | Chelsea | | Middlesbrough | | 2:0 (1:0) |
| London |
FA Cup 1995/96, Fourth Round Proper |
| 13.02.1996 | | Wimbledon | | Middlesbrough | | 1:0 (0:0) * |
| London |
FA Cup 1994/95, Third Round Proper |
| 17.01.1995 | | Middlesbrough | | Swansea City | | 1:2 (0:1) * |
| Middlesbrough |
FA Cup 1993/94, Third Round Proper |
| 19.01.1994 | | Middlesbrough | | Cardiff City | | 1:2 aet (0:1, 1:1) * |
| Middlesbrough |
FA Cup 1992/93, Fourth Round Proper |
| 03.02.1993 | | Middlesbrough | | Nottingham Forest | | 0:3 (0:2) * |
| Middlesbrough |
FA Cup 1991/92, Fifth Round Proper |
| 26.02.1992 | | Middlesbrough | | Portsmouth | | 2:4 * |
| Middlesbrough |
FA Cup 1990/91, Fourth Round Proper |
| 26.01.1991 | | Cambridge United | | Middlesbrough | | 2:0 |
| Cambridge |
FA Cup 1989/90, Third Round Proper |
| 17.01.1990 | | Everton | | Middlesbrough | | 1:0 * |
| Liverpool |
FA Cup 1988/89, Third Round Proper |
| 07.01.1989 | | Middlesbrough | | Grimsby Town | | 1:2 (1:0) |
| Middlesbrough |
FA Cup 1987/88, Fourth Round Proper |
| 09.02.1988 | | Everton | | Middlesbrough | | 2:1 (1:0) * |
| Liverpool |
FA Cup 1986/87, Third Round Proper |
| 10.01.1987 | | Middlesbrough | | Preston North End | | 0:1 (0:1) |
| Middlesbrough |
FA Cup 1985/86, Third Round Proper |
| 13.01.1986 | | Middlesbrough | | Southampton | | 1:3 |
| |
FA Cup 1984/85, Third Round Proper |
| 08.01.1985 | | Darlington | | Middlesbrough | | 2:1 * |
| |
FA Cup 1983/84, Fifth Round Proper |
| 18.02.1984 | | Notts County | | Middlesbrough | | 1:0 |
| |
FA Cup 1982/83, Fifth Round Proper |
| 28.02.1983 | | Arsenal | | Middlesbrough | | 3:2 * |
| |
FA Cup 1981/82, Third Round Proper |
| 18.01.1982 | | Middlesbrough | | Queens Park Rangers | | 2:3 * |
| |
FA Cup 1980/81, Sixth Round Proper |
| 10.03.1981 | | Wolverhampton Wanderers | | Middlesbrough | | 3:1 * |
| |
FA Cup 1979/80, Fourth Round Proper |
| 26.01.1980 | | Birmingham City | | Middlesbrough | | 2:1 |
| |
FA Cup 1978/79, Third Round Proper |
| 15.01.1979 | | Crystal Palace | | Middlesbrough | | 1:0 * |
| |
FA Cup 1977/78, Sixth Round Proper |
| 14.03.1978 | | Orient | | Middlesbrough | | 2:1 * |
| |
FA Cup 1976/77, Sixth Round Proper |
| 19.03.1977 | | Liverpool | | Middlesbrough | | 2:0 |
| Liverpool |
FA Cup 1975/76, Third Round Proper |
| 06.01.1976 | | Bury | | Middlesbrough | | 3:2 * |
| |
FA Cup 1974/75, Sixth Round Proper |
| 08.03.1975 | | Birmingham City | | Middlesbrough | | 1:0 |
| Birmingham |
FA Cup 1973/74, Fourth Round Proper |
| 26.01.1974 | | Wrexham | | Middlesbrough | | 1:0 |
| |
FA Cup 1972/73, Third Round Proper |
| 13.01.1973 | | Plymouth Argyle | | Middlesbrough | | 1:0 |
| |
FA Cup 1971/72, Fifth Round Proper |
| 29.02.1972 | | Middlesbrough | | Manchester United | | 0:3 * |
| |
FA Cup 1970/71, Fourth Round Proper |
| 23.01.1971 | | Everton | | Middlesbrough | | 3:0 |
| Liverpool |
FA Cup 1969/70, Sixth Round Proper |
| 25.02.1970 | | Manchester United | | Middlesbrough | | 2:1 (1:0) * |
| |
FA Cup 1968/69, Third Round Proper |
| 06.01.1969 | | Millwall | | Middlesbrough | | 1:0 * |
| |
FA Cup 1967/68, Fourth Round Proper |
| 20.02.1968 | | Bristol City | | Middlesbrough | | 2:1 * |
| |
FA Cup 1966/67, Third Round Proper |
| 28.01.1967 | | Mansfield Town | | Middlesbrough | | 2:0 |
| |
FA Cup 1965/66, Third Round Proper |
| 22.01.1966 | | Tottenham Hotspur | | Middlesbrough | | 4:0 |
| |
FA Cup 1964/65, Fifth Round Proper |
| 20.02.1965 | | Middlesbrough | | Leicester City | | 0:3 |
| |
FA Cup 1963/64, Third Round Proper |
| 04.01.1964 | | Brentford | | Middlesbrough | | 2:1 |
| |
FA Cup 1962/63, Fourth Round Proper |
| 16.03.1963 | | Middlesbrough | | Leeds United | | 0:2 |
| |
FA Cup 1961/62, Fifth Round Proper |
| 17.02.1962 | | Blackburn Rovers | | Middlesbrough | | 2:1 |
| |
FA Cup 1960/61, Third Round Proper |
| 07.01.1961 | | Manchester United | | Middlesbrough | | 3:0 |
| |
FA Cup 1959/60, Third Round Proper |
| 09.01.1960 | | Sheffield Wednesday | | Middlesbrough | | 2:1 |
| |
FA Cup 1958/59, Third Round Proper |
| 24.01.1959 | | Middlesbrough | | Birmingham City | | 0:1 |
| |
FA Cup 1957/58, Fourth Round Proper |
| 25.01.1958 | | Stoke City | | Middlesbrough | | 3:1 |
| |
FA Cup 1956/57, Fourth Round Proper |
| 26.01.1957 | | Middlesbrough | | Aston Villa | | 2:3 |
| |
FA Cup 1955/56, Fourth Round Proper |
| 28.01.1956 | | Tottenham Hotspur | | Middlesbrough | | 3:1 |
| |
FA Cup 1954/55, Third Round Proper |
| 08.01.1955 | | Middlesbrough | | Notts County | | 1:4 |
| |
FA Cup 1953/54, Third Round Proper |
| 14.01.1954 | | Leicester City | | Middlesbrough | | 3:2 * |
| |
FA Cup 1952/53, Third Round Proper |
| 10.01.1953 | | Aston Villa | | Middlesbrough | | 3:1 |
| |
FA Cup 1951/52, Fourth Round Proper |
| 06.02.1952 | | Middlesbrough | | Doncaster Rovers | | 1:4 |
| |
FA Cup 1950/51, Third Round Proper |
| 06.01.1951 | | Leeds United | | Middlesbrough | | 1:0 |
| |
FA Cup 1949/50, Fourth Round Proper |
| 28.01.1950 | | Chesterfield | | Middlesbrough | | 3:2 |
| |
FA Cup 1948/49, Third Round Proper |
| 08.01.1949 | | Brentford | | Middlesbrough | | 3:2 |
| |
FA Cup 1947/48, Fifth Round Proper |
| 07.02.1948 | | Middlesbrough | | Derby County | | 1:2 |
| |
FA Cup 1946/47, Sixth Round Proper |
| 04.03.1947 | | Burnley | | Middlesbrough | | 1:0 * |
| |
FA Cup 1945/46, Fifth Round Proper |
| 09.02.1946 | | Bolton Wanderers | | Middlesbrough | | 1:0 |
| |
FA Cup 1945/46, Fourth Round Proper |
| 26.01.1946 | | Blackpool | | Middlesbrough | | 3:2 |
| |
FA Cup 1938/39, Fourth Round Proper |
| 21.01.1939 | | Middlesbrough | | Sunderland | | 0:2 |
| |
FA Cup 1937/38, Fifth Round Proper |
| 12.02.1938 | | York City | | Middlesbrough | | 1:0 |
| |
FA Cup 1936/37, Third Round Proper |
| 16.01.1937 | | Wolverhampton Wanderers | | Middlesbrough | | 6:1 |
| |
FA Cup 1935/36, Sixth Round Proper |
| 29.02.1936 | | Grimsby Town | | Middlesbrough | | 3:1 |
| |
FA Cup 1934/35, Third Round Proper |
| 17.01.1935 | | Blackburn Rovers | | Middlesbrough | | 1:0 * |
| |
FA Cup 1933/34, Third Round Proper |
| 17.01.1934 | | Middlesbrough | | Sunderland | | 1:2 * |
| |
FA Cup 1932/33, Fifth Round Proper |
| 22.02.1933 | | Birmingham | | Middlesbrough | | 3:0 * |
| |
FA Cup 1931/32, Third Round Proper |
| 13.01.1932 | | Portsmouth | | Middlesbrough | | 3:0 * |
| |
FA Cup 1930/31, Third Round Proper |
| 19.01.1931 | | Bradford City | | Middlesbrough | | 2:1 * |
| |
FA Cup 1929/30, Fifth Round Proper |
| 15.02.1930 | | Middlesbrough | | Arsenal | | 0:2 |
| |
FA Cup 1928/29, Fourth Round Proper |
| 26.01.1929 | | West Bromwich Albion | | Middlesbrough | | 1:0 |
| |
FA Cup 1927/28, Fifth Round Proper |
| 18.02.1928 | | Huddersfield Town | | Middlesbrough | | 4:0 |
| |
FA Cup 1926/27, Fifth Round Proper |
| 19.02.1927 | | Millwall | | Middlesbrough | | 3:2 |
| |
FA Cup 1925/26, Fourth Round Proper |
| 30.01.1926 | | Clapton Orient | | Middlesbrough | | 4:2 |
| |
FA Cup 1924/25, First Round Proper |
| 10.01.1925 | | Bradford Park Avenue | | Middlesbrough | | 1:0 |
| |
FA Cup 1923/24, First Round Proper |
| 12.01.1924 | | Middlesbrough | | Watford | | 0:1 |
| |
FA Cup 1922/23, Second Round Proper |
| 08.02.1923 | | Sheffield United | | Middlesbrough | | 3:0 * |
| |
FA Cup 1921/22, First Round Proper |
| 07.01.1922 | | Hull City | | Middlesbrough | | 5:0 |
| |
FA Cup 1920/21, First Round Proper |
| 08.01.1921 | | Derby County | | Middlesbrough | | 2:0 |
| |
FA Cup 1919/20, Second Round Proper |
| 31.01.1920 | | Notts County | | Middlesbrough | | 1:0 |
| |
FA Cup 1914/15, Second Round Proper |
| 30.01.1915 | | Bradford City | | Middlesbrough | | 1:0 |
| |
FA Cup 1913/14, First Round Proper |
| 10.01.1914 | | Blackburn Rovers | | Middlesbrough | | 3:0 |
| |
FA Cup 1912/13, Third Round Proper |
| 22.02.1913 | | Burnley | | Middlesbrough | | 3:1 |
| |
FA Cup 1911/12, Second Round Proper |
| 08.02.1912 | | West Ham United | | Middlesbrough | | 2:1 * |
| |
FA Cup 1910/11, Third Round Proper |
| 25.02.1911 | | Middlesbrough | | Blackburn Rovers | | 0:3 |
| |
FA Cup 1909/10, First Round Proper |
| 19.01.1910 | | Everton | | Middlesbrough | | 5:3 * |
| |
FA Cup 1908/09, First Round Proper |
| 16.01.1909 | | Preston North End | | Middlesbrough | | 1:0 |
| |
FA Cup 1907/08, First Round Proper |
| 11.01.1908 | | Notts County | | Middlesbrough | | 2:0 |
| |
FA Cup 1906/07, Second Round Proper |
| 02.02.1907 | | Brentford | | Middlesbrough | | 1:0 |
| |
FA Cup 1905/06, Third Round Proper |
| 24.02.1906 | | Southampton | | Middlesbrough | | 6:1 |
| |
FA Cup 1904/05, First Round Proper |
| 09.02.1905 | | Tottenham Hotspur | | Middlesbrough | | 1:0 * |
| |
FA Cup 1903/04, Third Round Proper |
| 09.03.1904 | | Middlesbrough | | Manchester City | | 1:3 * |
| |
FA Cup 1902/03, Intermediate Round |
| 13.12.1902 | | Bristol City | | Middlesbrough | | 3:1 |
| |
FA Cup 1901/02, First Round Proper |
| 29.01.1902 | | Bristol Rovers | | Middlesbrough | | 1:0 * |
| |
FA Cup 1900/01, Third Round Proper |
| 23.03.1901 | | Middlesbrough | | West Bromwich Albion | | 0:1 |
| |
FA Cup 1894/95, Second Round Proper |
| 16.02.1895 | | Sheffield Wednesday | | Middlesbrough | | 6:1 |
| |
FA Cup 1893/94, First Round Proper |
| 27.01.1894 | | Newton Heath | | Middlesbrough | | 4:0 |
| |
FA Cup 1892/93, Second Round Proper |
| 04.02.1893 | | Wolverhampton Wanderers | | Middlesbrough | | 2:1 |
| |
FA Cup 1891/92, Second Round |
| 30.01.1892 | | Middlesbrough | | Preston North End | | 1:2 |
| |
FA Cup 1887/88, Sixth Round |
| 28.01.1888 | | Middlesbrough | | Crewe Alexandra | | 0:2 |
| |
FA Cup 1887/88, Third Round |
| 03.12.1887 | | Sunderland | | Middlesbrough | | 4:2 * |
| |
FA Cup 1886/87, Second Round |
| 27.11.1886 | | Lincoln City | | Middlesbrough | | 2:0 * |
| |
FA Cup 1885/86, Fifth Round |
| 23.01.1886 | | Redcar | | Middlesbrough | | 2:1 |
| |
FA Cup 1884/85, Fourth Round |
| 24.01.1885 | | Old Etonians | | Middlesbrough | | 5:2 |
| |
FA Cup 1883/84, First Round |
| 10.11.1883 | | Middlesbrough | | Staveley | | 1:5 |
| |