FA Cup 2021/22, Fifth Round Proper |
| 01.03.2022 | | Middlesbrough | | Tottenham Hotspur | | 1:0 aet (0:0, 0:0) |
| Middlesbrough |
FA Cup 2021/22, Third Round Proper |
| 08.01.2022 | | Mansfield Town | | Middlesbrough | | 2:3 (0:2) |
| Mansfield |
FA Cup 2018/19, Third Round Proper |
| 05.01.2019 | | Middlesbrough | | Peterborough United | | 5:0 (0:0) |
| Middlesbrough |
FA Cup 2017/18, Third Round Proper |
| 06.01.2018 | | Middlesbrough | | Sunderland | | 2:0 (2:0) |
| Middlesbrough |
FA Cup 2016/17, Fifth Round Proper |
| 18.02.2017 | | Middlesbrough | | Oxford United | | 3:2 (2:0) |
| Middlesbrough |
FA Cup 2016/17, Fourth Round Proper |
| 28.01.2017 | | Middlesbrough | | Accrington Stanley | | 1:0 (0:0) |
| Middlesbrough |
FA Cup 2016/17, Third Round Proper |
| 08.01.2017 | | Middlesbrough | | Sheffield Wednesday | | 3:0 (0:0) |
| Middlesbrough |
FA Cup 2014/15, Fourth Round Proper |
| 24.01.2015 | | Manchester City | | Middlesbrough | | 0:2 (0:0) |
| Manchester |
FA Cup 2014/15, Third Round Proper |
| 03.01.2015 | | Barnsley | | Middlesbrough | | 0:2 (0:0) |
| Barnsley |
FA Cup 2012/13, Fourth Round Proper |
| 26.01.2013 | | Middlesbrough | | Aldershot Town | | 2:1 (0:0) |
| Middlesbrough |
FA Cup 2012/13, Third Round Proper |
| 05.01.2013 | | Middlesbrough | | Hastings United | | 4:1 (1:0) |
| Middlesbrough |
FA Cup 2011/12, Third Round Proper |
| 07.01.2012 | | Middlesbrough | | Shrewsbury Town | | 1:0 (1:0) |
| Middlesbrough |
FA Cup 2008/09, Fifth Round Proper |
| 25.02.2009 | | Middlesbrough | | West Ham United | | 2:0 (2:0) * |
| Middlesbrough |
FA Cup 2008/09, Fourth Round Proper |
| 24.01.2009 | | Wolverhampton Wanderers | | Middlesbrough | | 1:2 (0:1) |
| Wolverhampton |
FA Cup 2008/09, Third Round Proper |
| 03.01.2009 | | Middlesbrough | | Barrow | | 2:1 (1:0) |
| Middlesbrough |
FA Cup 2007/08, Fifth Round Proper |
| 27.02.2008 | | Middlesbrough | | Sheffield United | | 1:0 aet (0:0) * |
| Middlesbrough |
FA Cup 2007/08, Fourth Round Proper |
| 26.01.2008 | | Mansfield Town | | Middlesbrough | | 0:2 (0:1) |
| Mansfield |
FA Cup 2007/08, Third Round Proper |
| 05.01.2008 | | Bristol City | | Middlesbrough | | 1:2 (1:1) |
| Bristol |
FA Cup 2006/07, Third Round Proper |
| 16.01.2007 | | Middlesbrough | | Hull City | | 4:3 (1:0) * |
| Middlesbrough |
FA Cup 2005/06, Sixth Round Proper |
| 12.04.2006 | | Middlesbrough | | Charlton Athletic | | 4:2 (2:1) * |
| Middlesbrough |
FA Cup 2005/06, Fifth Round Proper |
| 19.02.2006 | | Preston North End | | Middlesbrough | | 0:2 (0:0) |
| Preston |
FA Cup 2005/06, Fourth Round Proper |
| 08.02.2006 | | Middlesbrough | | Coventry City | | 1:0 (1:0) * |
| Middlesbrough |
FA Cup 2005/06, Third Round Proper |
| 17.01.2006 | | Middlesbrough | | Nuneaton Borough | | 5:2 (2:0) * |
| Middlesbrough |
FA Cup 2004/05, Third Round Proper |
| 08.01.2005 | | Notts County | | Middlesbrough | | 1:2 (1:0) |
| Nottingham |
FA Cup 2003/04, Third Round Proper |
| 03.01.2004 | | Middlesbrough | | Notts County | | 2:0 (1:0) |
| Middlesbrough |
FA Cup 2001/02, Sixth Round Proper |
| 10.03.2002 | | Middlesbrough | | Everton | | 3:0 (3:0) |
| Middlesbrough |
FA Cup 2001/02, Fifth Round Proper |
| 16.02.2002 | | Middlesbrough | | Blackburn Rovers | | 1:0 (0:0) |
| Middlesbrough |
FA Cup 2001/02, Fourth Round Proper |
| 26.01.2002 | | Middlesbrough | | Manchester United | | 2:0 (0:0) |
| Middlesbrough |
FA Cup 2001/02, Third Round Proper |
| 15.01.2002 | | Middlesbrough | | Wimbledon | | 2:0 (1:0) * |
| Middlesbrough |
FA Cup 2000/01, Third Round Proper |
| 08.01.2001 | | Bradford City | | Middlesbrough | | 0:1 (0:0) |
| Bradford |
FA Cup 1997/98, Third Round Proper |
| 13.01.1998 | | Middlesbrough | | Queens Park Rangers | | 2:0 (0:0) * |
| Middlesbrough |
FA Cup 1996/97, Semi Final |
| 22.04.1997 | | Middlesbrough | | Chesterfield | | 3:0 (1:0) * |
| Sheffield |
FA Cup 1996/97, Sixth Round Proper |
| 08.03.1997 | | Derby County | | Middlesbrough | | 0:2 (0:1) |
| Derby |
FA Cup 1996/97, Fifth Round Proper |
| 15.02.1997 | | Manchester City | | Middlesbrough | | 0:1 (0:0) |
| Manchester |
FA Cup 1996/97, Fourth Round Proper |
| 25.01.1997 | | Hednesford Town | | Middlesbrough | | 2:3 (1:1) |
| Middlesbrough |
FA Cup 1996/97, Third Round Proper |
| 04.01.1997 | | Middlesbrough | | Chester City | | 6:0 (3:0) |
| Middlesbrough |
FA Cup 1995/96, Third Round Proper |
| 06.01.1996 | | Notts County | | Middlesbrough | | 1:2 (0:0) |
| Nottingham |
FA Cup 1992/93, Third Round Proper |
| 13.01.1993 | | Middlesbrough | | Chelsea | | 2:1 (0:0) |
| Middlesbrough |
FA Cup 1991/92, Fourth Round Proper |
| 04.02.1992 | | Sheffield Wednesday | | Middlesbrough | | 1:2 |
| Sheffield |
FA Cup 1991/92, Third Round Proper |
| 04.01.1992 | | Middlesbrough | | Manchester City | | 2:1 |
| Middlesbrough |
FA Cup 1990/91, Third Round Proper |
| 14.01.1991 | | Plymouth Argyle | | Middlesbrough | | 1:2 * |
| Plymouth |
FA Cup 1987/88, Third Round Proper |
| 12.01.1988 | | Middlesbrough | | Sutton United | | 1:0 aet * |
| Middlesbrough |
FA Cup 1986/87, Second Round Proper |
| 07.12.1986 | | Notts County | | Middlesbrough | | 0:1 (0:0) |
| Nottingham |
FA Cup 1986/87, First Round Proper |
| 15.11.1986 | | Middlesbrough | | Blackpool | | 3:0 (1:0) |
| Middlesbrough |
FA Cup 1983/84, Fourth Round Proper |
| 31.01.1984 | | Middlesbrough | | Bournemouth | | 2:0 |
| |
FA Cup 1983/84, Third Round Proper |
| 07.01.1984 | | Middlesbrough | | Arsenal | | 3:2 |
| |
FA Cup 1982/83, Fourth Round Proper |
| 29.01.1983 | | Middlesbrough | | Notts County | | 2:0 |
| |
FA Cup 1982/83, Third Round Proper |
| 11.01.1983 | | Bishop's Stortford | | Middlesbrough | | 1:2 * |
| |
FA Cup 1980/81, Fifth Round Proper |
| 14.02.1981 | | Middlesbrough | | Barnsley | | 2:1 |
| |
FA Cup 1980/81, Fourth Round Proper |
| 24.01.1981 | | Middlesbrough | | West Bromwich Albion | | 1:0 |
| |
FA Cup 1980/81, Third Round Proper |
| 03.01.1981 | | Swansea City | | Middlesbrough | | 0:5 |
| |
FA Cup 1979/80, Third Round Proper |
| 14.01.1980 | | Middlesbrough | | Portsmouth | | 3:0 * |
| |
FA Cup 1977/78, Fifth Round Proper |
| 27.02.1978 | | Middlesbrough | | Bolton Wanderers | | 2:0 |
| |
FA Cup 1977/78, Fourth Round Proper |
| 28.01.1978 | | Middlesbrough | | Everton | | 3:2 |
| |
FA Cup 1977/78, Third Round Proper |
| 07.01.1978 | | Middlesbrough | | Coventry City | | 3:0 |
| |
FA Cup 1976/77, Fifth Round Proper |
| 26.02.1977 | | Middlesbrough | | Arsenal | | 4:1 |
| Middlesbrough |
FA Cup 1976/77, Fourth Round Proper |
| 29.01.1977 | | Middlesbrough | | Hereford United | | 4:0 |
| Middlesbrough |
FA Cup 1976/77, Third Round Proper |
| 11.01.1977 | | Middlesbrough | | Wimbledon | | 1:0 * |
| Middlesbrough |
FA Cup 1974/75, Fifth Round Proper |
| 18.02.1975 | | Middlesbrough | | Peterborough United | | 2:0 * |
| |
FA Cup 1974/75, Fourth Round Proper |
| 25.01.1975 | | Middlesbrough | | Sunderland | | 3:1 |
| |
FA Cup 1974/75, Third Round Proper |
| 07.01.1975 | | Middlesbrough | | Wycombe Wanderers | | 1:0 * |
| |
FA Cup 1973/74, Third Round Proper |
| 05.01.1974 | | Grantham | | Middlesbrough | | 0:2 |
| |
FA Cup 1971/72, Fourth Round Proper |
| 08.02.1972 | | Middlesbrough | | Millwall | | 2:1 * |
| |
FA Cup 1971/72, Third Round Proper |
| 18.01.1972 | | Middlesbrough | | Manchester City | | 1:0 * |
| |
FA Cup 1970/71, Third Round Proper |
| 05.01.1971 | | Middlesbrough | | Manchester United | | 2:1 * |
| |
FA Cup 1969/70, Fifth Round Proper |
| 07.02.1970 | | Carlisle United | | Middlesbrough | | 1:2 (0:0) |
| |
FA Cup 1969/70, Fourth Round Proper |
| 24.01.1970 | | Middlesbrough | | York City | | 4:1 (1:0) |
| |
FA Cup 1969/70, Third Round Proper |
| 03.01.1970 | | Middlesbrough | | West Ham United | | 2:1 (1:0) |
| |
FA Cup 1967/68, Third Round Proper |
| 07.02.1968 | | Middlesbrough | | Hull City | | 1:0 * |
| York |
FA Cup 1966/67, Second Round Proper |
| 16.01.1967 | | Middlesbrough | | York City | | 4:1 * |
| |
FA Cup 1966/67, First Round Proper |
| 26.11.1966 | | Chester | | Middlesbrough | | 2:5 |
| |
FA Cup 1964/65, Fourth Round Proper |
| 01.02.1965 | | Middlesbrough | | Charlton Athletic | | 2:1 * |
| |
FA Cup 1964/65, Third Round Proper |
| 09.01.1965 | | Middlesbrough | | Oldham Athletic | | 6:2 |
| |
FA Cup 1962/63, Third Round Proper |
| 11.03.1963 | | Middlesbrough | | Blackburn Rovers | | 3:1 * |
| |
FA Cup 1961/62, Fourth Round Proper |
| 31.01.1962 | | Middlesbrough | | Shrewsbury Town | | 5:1 * |
| |
FA Cup 1961/62, Third Round Proper |
| 10.01.1962 | | Middlesbrough | | Cardiff City | | 1:0 |
| |
FA Cup 1957/58, Third Round Proper |
| 04.01.1958 | | Middlesbrough | | Derby County | | 5:0 |
| |
FA Cup 1956/57, Third Round Proper |
| 10.01.1957 | | Charlton Athletic | | Middlesbrough | | 2:3 * |
| |
FA Cup 1955/56, Third Round Proper |
| 07.01.1956 | | Bradford Park Avenue | | Middlesbrough | | 0:4 |
| |
FA Cup 1951/52, Third Round Proper |
| 16.01.1952 | | Derby County | | Middlesbrough | | 0:2 * |
| |
FA Cup 1949/50, Third Round Proper |
| 16.01.1950 | | Aston Villa | | Middlesbrough | | 0:3 * |
| |
FA Cup 1947/48, Fourth Round Proper |
| 24.01.1948 | | Brentford | | Middlesbrough | | 1:2 |
| |
FA Cup 1947/48, Third Round Proper |
| 10.01.1948 | | Hull City | | Middlesbrough | | 1:3 |
| |
FA Cup 1946/47, Fifth Round Proper |
| 12.02.1947 | | Middlesbrough | | Nottingham Forest | | 6:2 * |
| |
FA Cup 1946/47, Fourth Round Proper |
| 25.01.1947 | | Middlesbrough | | Chesterfield | | 2:1 |
| |
FA Cup 1946/47, Third Round Proper |
| 15.01.1947 | | Middlesbrough | | Queens Park Rangers | | 3:1 * |
| |
FA Cup 1945/46, Fourth Round Proper |
| 04.02.1946 | | Blackpool | | Middlesbrough | | 0:1 * |
| |
FA Cup 1945/46, Fourth Round Proper |
| 30.01.1946 | | Middlesbrough | | Blackpool | | 3:2 |
| |
FA Cup 1945/46, Third Round Proper |
| 09.01.1946 | | Middlesbrough | | Leeds United | | 7:2 |
| |
FA Cup 1938/39, Third Round Proper |
| 16.01.1939 | | Bolton Wanderers | | Middlesbrough | | 0:1 * |
| |
FA Cup 1937/38, Fourth Round Proper |
| 22.01.1938 | | Nottingham Forest | | Middlesbrough | | 1:3 |
| |
FA Cup 1937/38, Third Round Proper |
| 08.01.1938 | | Middlesbrough | | Stockport County | | 2:0 |
| |
FA Cup 1935/36, Fifth Round Proper |
| 15.02.1936 | | Middlesbrough | | Leicester City | | 2:1 |
| |
FA Cup 1935/36, Fourth Round Proper |
| 25.01.1936 | | Middlesbrough | | Clapton Orient | | 3:0 |
| |
FA Cup 1935/36, Third Round Proper |
| 11.01.1936 | | Middlesbrough | | Southampton | | 1:0 |
| |
FA Cup 1932/33, Fourth Round Proper |
| 28.01.1933 | | Middlesbrough | | Stoke City | | 4:1 |
| |
FA Cup 1932/33, Third Round Proper |
| 14.01.1933 | | Manchester United | | Middlesbrough | | 1:4 |
| |
FA Cup 1929/30, Fourth Round Proper |
| 03.02.1930 | | Middlesbrough | | Charlton Athletic | | 1:0 * |
| |
FA Cup 1929/30, Third Round Proper |
| 15.01.1930 | | Middlesbrough | | Chesterfield | | 4:3 * |
| |
FA Cup 1928/29, Third Round Proper |
| 21.01.1929 | | Middlesbrough | | Walsall | | 5:1 * |
| |
FA Cup 1927/28, Fourth Round Proper |
| 28.01.1928 | | Southport | | Middlesbrough | | 0:3 |
| |
FA Cup 1927/28, Third Round Proper |
| 14.01.1928 | | Middlesbrough | | South Shields | | 3:0 |
| |
FA Cup 1926/27, Fourth Round Proper |
| 29.01.1927 | | Preston North End | | Middlesbrough | | 0:3 |
| |
FA Cup 1926/27, Third Round Proper |
| 08.01.1927 | | Middlesbrough | | Leicester City | | 5:3 |
| |
FA Cup 1925/26, Third Round Proper |
| 09.01.1926 | | Middlesbrough | | Leeds United | | 5:1 |
| |
FA Cup 1922/23, First Round Proper |
| 13.01.1923 | | Oldham Athletic | | Middlesbrough | | 0:1 |
| |
FA Cup 1919/20, First Round Proper |
| 14.01.1920 | | Middlesbrough | | Lincoln City | | 4:1 |
| |
FA Cup 1914/15, First Round Proper |
| 09.01.1915 | | Middlesbrough | | Goole Town | | 9:3 |
| |
FA Cup 1912/13, Second Round Proper |
| 01.02.1913 | | Middlesbrough | | Queens Park Rangers | | 3:2 |
| |
FA Cup 1912/13, First Round Proper |
| 15.01.1913 | | Middlesbrough | | Millwall | | 4:1 * |
| |
FA Cup 1911/12, First Round Proper |
| 25.01.1912 | | Sheffield Wednesday | | Middlesbrough | | 1:2 * |
| |
FA Cup 1910/11, Second Round Proper |
| 08.02.1911 | | Leicester Fosse | | Middlesbrough | | 1:2 * |
| |
FA Cup 1910/11, First Round Proper |
| 14.01.1911 | | Middlesbrough | | Glossop | | 1:0 |
| |
FA Cup 1906/07, First Round Proper |
| 12.01.1907 | | Middlesbrough | | Northampton Town | | 4:2 |
| |
FA Cup 1905/06, Second Round Proper |
| 12.02.1906 | | Brighton & Hove Albion | | Middlesbrough | | 1:3 * |
| |
FA Cup 1905/06, First Round Proper |
| 13.01.1906 | | Middlesbrough | | Bolton Wanderers | | 3:0 |
| |
FA Cup 1903/04, Second Round Proper |
| 20.02.1904 | | Preston North End | | Middlesbrough | | 0:3 |
| |
FA Cup 1903/04, First Round Proper |
| 06.02.1904 | | Millwall | | Middlesbrough | | 0:2 |
| |
FA Cup 1900/01, Second Round Proper |
| 23.02.1901 | | Middlesbrough | | Kettering | | 5:0 |
| |
FA Cup 1900/01, First Round Proper |
| 09.02.1901 | | Middlesbrough | | Newcastle United | | 3:1 |
| |
FA Cup 1900/01, Intermediate Round |
| 05.01.1901 | | Grimsby Town | | Middlesbrough | | 0:1 |
| |
FA Cup 1894/95, First Round Proper |
| 02.02.1895 | | Middlesbrough | | Chesterfield | | 4:0 |
| |
FA Cup 1892/93, First Round Proper |
| 21.01.1893 | | Newcastle United | | Middlesbrough | | 2:3 |
| |
FA Cup 1891/92, First Round |
| 16.01.1892 | | Luton Town | | Middlesbrough | | 0:3 |
| |
FA Cup 1887/88, Fifth Round |
| 07.01.1888 | | Middlesbrough | | Old Foresters | | 4:0 |
| |
FA Cup 1887/88, Second Round |
| 05.11.1887 | | Middlesbrough | | South Bank | | 4:1 |
| |
FA Cup 1887/88, First Round |
| 15.10.1887 | | Middlesbrough | | Whitburn | | 4:0 |
| |
FA Cup 1886/87, First Round |
| 30.10.1886 | | Bishop Auckland Church Institute | | Middlesbrough | | 0:1 |
| |
FA Cup 1885/86, Third Round |
| 19.12.1885 | | Middlesbrough | | Grimsby Town | | 2:1 |
| |
FA Cup 1885/86, Second Round |
| 21.11.1885 | | Gainsborough Trinity | | Middlesbrough | | 1:2 |
| |
FA Cup 1884/85, Second Round |
| 06.12.1884 | | Middlesbrough | | Newark | | 4:1 |
| |
FA Cup 1885/86, First Round |
| | | Middlesbrough | | Horncastle | | +:- |
| |
FA Cup 1884/85, First Round |
| | | Middlesbrough | | Grimsby District | | +:- |
| |