| Season | Competition |
Round Reached | Date |
Home | |
Away |
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| 2007/2008 | F.A. Cup | 6th Round | Sun 09 Mar | Middlesbrough | 0 - 2 | Cardiff City |
| League Cup | 3rd Round | Wed 26 Sep | Tottenham H. | 2 - 0 | Middlesbrough |
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| 2006/2007 | F.A. Cup | Quarter Final Replay | Mon 19 Mar | Man. Utd. | 1 - 0 | Middlesbrough |
| League Cup | 2nd Round | Wed 20 Sep | Middlesbrough | 0 - 1 | Notts. County |
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| 2005/2006 | UEFA Cup | Final | Wed 10 May | Middlesbrough | 0 - 4 | Seville |
| played in Eindhoven |
| F.A. Cup | Semi Final | Sun 23 Apr | Middlesbrough | 0 - 1 | West Ham Utd. |
| played at Aston Villa |
| League Cup | Quarter Final | Wed 21 Dec | Middlesbrough | 0 - 1 | Blackburn R. |
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| 2004/2005 | UEFA Cup | Last 16 Knockout Stage | Thu 17 Mar | Sport. Lisbon | 1 - 0 | Middlesbrough |
| Sporting Lisbon win 4-2 on aggregate |
| F.A. Cup | 4th Round | Sat 29 Jan | Man. Utd. | 3 - 0 | Middlesbrough |
| League Cup | 4th Round | Wed 10 Nov | Liverpool | 2 - 0 | Middlesbrough |
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| 2003/2004 | F.A. Cup | 4th Round | Sat 24 Jan | Arsenal | 4 - 1 | Middlesbrough |
| League Cup | Final | Sun 29 Feb | Middlesbrough | 2 - 1 | Bolton Wdrs. |
| played at Millennium Stadium, Cardiff |
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| 2002/2003 | F.A. Cup | 3rd Round | Sat 04 Jan | Chelsea | 1 - 0 | Middlesbrough |
| League Cup | 3rd Round | Wed 06 Nov | Ipswich Town | 3 - 1 | Middlesbrough |
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| 2001/2002 | F.A. Cup | Semi Final | Sun 14 Apr | Middlesbrough | 0 - 1 | Arsenal |
| played at Old Trafford |
| League Cup | 3rd Round | Wed 10 Oct | Blackburn R. | 2 - 1 | Middlesbrough |
| after extra time, 90 minutes 1-1 |
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| 2000/2001 | F.A. Cup | 4th Round Replay | Tue 13 Feb | Wimbledon | 3 - 1 | Middlesbrough |
| after extra time, 90 minutes 1-1 |
| League Cup | 3rd Round | Tue 31 Oct | Wimbledon | 1 - 0 | Middlesbrough |
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| 1999/2000 | F.A. Cup | 3rd Round | Sat 11 Dec | Wrexham | 2 - 1 | Middlesbrough |
| League Cup | Quarter Final | Tue 14 Dec | Tranmere Rvs. | 2 - 1 | Middlesbrough |
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| 1998/1999 | F.A. Cup | 3rd Round | Sun 03 Jan | Man. Utd. | 3 - 1 | Middlesbrough |
| League Cup | 3rd Round | Wed 28 Oct | Middlesbrough | 2 - 3 | Everton |
| after extra time, 90 minutes 1-1 |
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| 1997/1998 | F.A. Cup | 4th Round | Sat 24 Jan | Middlesbrough | 1 - 2 | Arsenal |
| League Cup | Final | Sun 29 Mar | Chelsea | 2 - 0 | Middlesbrough |
| after extra time, 90 minutes 0-0; played at Wembley |
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| 1996/1997 | F.A. Cup | Final | Sat 17 May | Chelsea | 2 - 0 | Middlesbrough |
| played at Wembley |
| League Cup | Final Replay | Wed 16 Apr | Leicester City | 1 - 0 | Middlesbrough |
| after extra time, 90 minutes 0-0; played at Hillsborough |
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| 1995/1996 | F.A. Cup | 4th Round Replay | Tue 13 Feb | Wimbledon | 1 - 0 | Middlesbrough |
| League Cup | 4th Round Replay | Wed 20 Dec | Birmingham C. | 2 - 0 | Middlesbrough |
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| 1994/1995 | F.A. Cup | 3rd Round Replay | Tue 17 Jan | Middlesbrough | 1 - 2 | Swansea City |
| League Cup | 3rd Round | Wed 26 Oct | Aston Villa | 1 - 0 | Middlesbrough |
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| 1993/1994 | F.A. Cup | 3rd Round Replay | Wed 19 Jan | Middlesbrough | 1 - 2 | Cardiff City |
| after extra time, 90 minutes 1-1 |
| League Cup | 3rd Round Replay | Wed 10 Nov | Sheff. Wed. | 2 - 1 | Middlesbrough |
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| 1992/1993 | F.A. Cup | 4th Round Replay | Wed 03 Feb | Middlesbrough | 0 - 3 | Nottm. Forest |
| League Cup | 2nd Round | Wed 07 Oct | Middlesbrough | 1 - 3 | Newcastle Utd. |
| Newcastle United won 3-1 on aggregate |
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| 1991/1992 | F.A. Cup | 5th Round Replay | Wed 26 Feb | Middlesbrough | 2 - 4 | Portsmouth |
| League Cup | Semi Final | Wed 11 Mar | Man. Utd. | 2 - 1 | Middlesbrough |
| Manchester United won 2-1 on aggregate |
| (Full Members) | Northern Section Quarter-Final | Tue 26 Nov | Middlesbrough | 0 - 1 | Tranmere Rvs. |
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| 1990/1991 | F.A. Cup | 4th Round | Sat 26 Jan | Cambridge U. | 2 - 0 | Middlesbrough |
| League Cup | 4th Round | Wed 28 Nov | Aston Villa | 3 - 2 | Middlesbrough |
| (Full Members) | Northern Section 2nd Round | Wed 19 Dec | Man. City | 2 - 1 | Middlesbrough |
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| 1989/1990 | F.A. Cup | 3rd Round 2nd Replay | Wed 17 Jan | Everton | 1 - 0 | Middlesbrough |
| League Cup | 3rd Round Replay | Wed 08 Nov | Wimbledon | 1 - 0 | Middlesbrough |
| (Full Members) | Final | Sun 25 Mar | Chelsea | 1 - 0 | Middlesbrough |
| at Wembley |
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| 1988/1989 | F.A. Cup | 3rd Round | Sat 07 Jan | Middlesbrough | 1 - 2 | Grimsby Town |
| League Cup | 2nd Round | Tue 11 Oct | Tranmere Rvs. | 1 - 0 | Middlesbrough |
| Tranmere Rovers won 1-0 on aggregate |
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| 1987/1988 | F.A. Cup | 4th Round 2nd Replay | Tue 09 Feb | Everton | 2 - 1 | Middlesbrough |
| League Cup | 2nd Round | Wed 07 Oct | Aston Villa | 1 - 0 | Middlesbrough |
| Aston Villa won 2-0 on aggregate |
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| 1986/1987 | F.A. Cup | 3rd Round | Sat 10 Jan | Middlesbrough | 0 - 1 | Preston N.E. |
| League Cup | 2nd Round | Tue 07 Oct | Birmingham C. | 3 - 2 | Middlesbrough |
| Birmingham City won 5-4 on aggregate |
| (Associate Members) | Northern Section Semi-Final | Tue 10 Mar | Middlesbrough | 0 - 1 | Mansfield Town |
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| 1985/1986 | F.A. Cup | 3rd Round | Mon 13 Jan | Middlesbrough | 1 - 3 | Southampton |
| League Cup | 1st Round | Tue 03 Sep | Middlesbrough | 4 - 4 | Mansfield Town |
| Mansfield Town won 6-4 on aggregate |
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| 1984/1985 | F.A. Cup | 3rd Round Replay | Tue 08 Jan | Darlington | 2 - 1 | Middlesbrough |
| League Cup | 1st Round | Tue 04 Sep | Middlesbrough | 2 - 2 | Bradford City |
| Bradford City won 4-2 on aggregate |
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| 1983/1984 | F.A. Cup | 5th Round | Sat 18 Feb | Notts. County | 1 - 0 | Middlesbrough |
| League Cup | 1st Round | Tue 13 Sep | Chesterfield | 0 - 1 | Middlesbrough |
| after extra time, aggregate 1-1, Chesterfield won 5-3 on penalties |
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| 1982/1983 | F.A. Cup | 5th Round Replay | Mon 28 Feb | Arsenal | 3 - 2 | Middlesbrough |
| League Cup | 2nd Round | Tue 26 Oct | Middlesbrough | 1 - 1 | Burnley |
| Burnley won 4-3 on aggregate |
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| 1981/1982 | F.A. Cup | 3rd Round Replay | Mon 18 Jan | Middlesbrough | 2 - 3 | Q.P.R. |
| after extra time, 90 minutes ?-? |
| League Cup | 3rd Round | Tue 10 Nov | Liverpool | 4 - 1 | Middlesbrough |
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| 1980/1981 | F.A. Cup | 6th Round Replay | Tue 10 Mar | Wolves | 3 - 1 | Middlesbrough |
| after extra time, 90 minutes ?-? |
| League Cup | 2nd Round | Tue 02 Sep | Ipswich Town | 3 - 0 | Middlesbrough |
| Ipswich Town won 4-3 on aggregate |
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| 1979/1980 | F.A. Cup | 4th Round | Sat 26 Jan | Birmingham C. | 2 - 1 | Middlesbrough |
| League Cup | 3rd Round | Tue 25 Sep | Middlesbrough | 1 - 3 | Nottm. Forest |
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| 1978/1979 | F.A. Cup | 3rd Round Replay | Mon 15 Jan | Crystal Palace | 1 - 0 | Middlesbrough |
| League Cup | 2nd Round Replay | Tue 05 Sep | Peterborough | 1 - 0 | Middlesbrough |
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| 1977/1978 | F.A. Cup | 6th Round Replay | Tue 14 Mar | Orient | 2 - 1 | Middlesbrough |
| League Cup | 3rd Round Replay | Mon 31 Oct | Middlesbrough | 1 - 2 | Everton |
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| 1976/1977 | F.A. Cup | 6th Round | Sat 19 Mar | Liverpool | 2 - 0 | Middlesbrough |
| League Cup | 2nd Round | Tue 31 Aug | Middlesbrough | 1 - 2 | Tottenham H. |
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| 1975/1976 | F.A. Cup | 3rd Round Replay | Tue 06 Jan | Bury | 3 - 2 | Middlesbrough |
| League Cup | Semi Final | Wed 21 Jan | Man. City | 4 - 0 | Middlesbrough |
| Manchester City won 4-1 on aggregate |
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| 1974/1975 | F.A. Cup | 6th Round | Sat 08 Mar | Birmingham C. | 1 - 0 | Middlesbrough |
| League Cup | Quarter Final Replay | Wed 18 Dec | Man. Utd. | 3 - 0 | Middlesbrough |
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| 1973/1974 | F.A. Cup | 4th Round | Sat 26 Jan | Wrexham | 1 - 0 | Middlesbrough |
| League Cup | 3rd Round Replay | Tue 06 Nov | Middlesbrough | 1 - 2 | Stoke City |
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| 1972/1973 | F.A. Cup | 3rd Round | Sat 13 Jan | Plymouth Arg. | 1 - 0 | Middlesbrough |
| League Cup | 3rd Round 2nd Replay | Mon 30 Oct | Tottenham H. | 2 - 1 | Middlesbrough |
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| 1971/1972 | F.A. Cup | 5th Round Replay | Tue 29 Feb | Middlesbrough | 0 - 3 | Man. Utd. |
| League Cup | 2nd Round Replay | Tue 14 Sep | Middlesbrough | 1 - 2 | York City |
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| 1970/1971 | F.A. Cup | 4th Round | Sat 23 Jan | Everton | 3 - 0 | Middlesbrough |
| League Cup | 3rd Round | Wed 07 Oct | Chelsea | 3 - 2 | Middlesbrough |
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| 1969/1970 | F.A. Cup | 6th Round Replay | Wed 25 Feb | Man. Utd. | 2 - 1 | Middlesbrough |
| League Cup | 2nd Round | Wed 03 Sep | Man. Utd. | 1 - 0 | Middlesbrough |
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| 1968/1969 | F.A. Cup | 3rd Round Replay | Mon 06 Jan | Millwall | 1 - 0 | Middlesbrough |
| League Cup | 2nd Round | Wed 04 Sep | Bristol City | 1 - 0 | Middlesbrough |
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| 1967/1968 | F.A. Cup | 4th Round Replay | Tue 20 Feb | Bristol City | 2 - 1 | Middlesbrough |
| League Cup | 3rd Round | Wed 11 Oct | Blackburn R. | 3 - 2 | Middlesbrough |
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| 1966/1967 | F.A. Cup | 3rd Round | Sat 28 Jan | Mansfield Town | 2 - 0 | Middlesbrough |
| League Cup | 1st Round Replay | Mon 29 Aug | York City | 2 - 1 | Middlesbrough |
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| 1965/1966 | F.A. Cup | 3rd Round | Sat 22 Jan | Tottenham H. | 4 - 0 | Middlesbrough |
| League Cup | 3rd Round Replay | Mon 18 Oct | Millwall | 3 - 1 | Middlesbrough |
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| 1964/1965 | F.A. Cup | 5th Round | Sat 20 Feb | Middlesbrough | 0 - 3 | Leicester City |
| League Cup | 2nd Round | Wed 23 Sep | Charlton Ath. | 2 - 1 | Middlesbrough |
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| 1963/1964 | F.A. Cup | 3rd Round | Sat 04 Jan | Brentford | 2 - 1 | Middlesbrough |
| League Cup | 2nd Round Replay | Wed 02 Oct | Middlesbrough | 2 - 3 | Bradford P.A. |
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| 1962/1963 | F.A. Cup | 4th Round | Sat 16 Mar | Middlesbrough | 0 - 2 | Leeds Utd. |
| League Cup | 2nd Round 2nd Replay | Wed 10 Oct | Hull City | 3 - 0 | Middlesbrough |
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| 1961/1962 | F.A. Cup | 5th Round | Sat 17 Feb | Blackburn R. | 2 - 1 | Middlesbrough |
| League Cup | 3rd Round | Wed 15 Nov | Norwich City | 3 - 2 | Middlesbrough |
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| 1960/1961 | F.A. Cup | 3rd Round | Sat 07 Jan | Man. Utd. | 3 - 0 | Middlesbrough |
| League Cup | 1st Round | Mon 03 Oct | Middlesbrough | 3 - 4 | Cardiff City |
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| 1959/1960 | F.A. Cup | 3rd Round | Sat 09 Jan | Sheff. Wed. | 2 - 1 | Middlesbrough |
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| 1958/1959 | F.A. Cup | 3rd Round | Sat 24 Jan | Middlesbrough | 0 - 1 | Birmingham C. |
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| 1957/1958 | F.A. Cup | 4th Round | Sat 25 Jan | Stoke City | 3 - 1 | Middlesbrough |
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| 1956/1957 | F.A. Cup | 4th Round | Sat 26 Jan | Middlesbrough | 2 - 3 | Aston Villa |
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| 1955/1956 | F.A. Cup | 4th Round | Sat 28 Jan | Tottenham H. | 3 - 1 | Middlesbrough |
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| 1954/1955 | F.A. Cup | 3rd Round | Sat 08 Jan | Middlesbrough | 1 - 4 | Notts. County |
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| 1953/1954 | F.A. Cup | 3rd Round Replay | Thu 14 Jan | Leicester City | 3 - 2 | Middlesbrough |
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| 1952/1953 | F.A. Cup | 3rd Round | Sat 10 Jan | Aston Villa | 3 - 1 | Middlesbrough |
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| 1951/1952 | F.A. Cup | 4th Round | Wed 06 Feb | Middlesbrough | 1 - 4 | Doncaster Rvs. |
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| 1950/1951 | F.A. Cup | 3rd Round | Sat 06 Jan | Leeds Utd. | 1 - 0 | Middlesbrough |
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| 1949/1950 | F.A. Cup | 4th Round | Sat 28 Jan | Chesterfield | 3 - 2 | Middlesbrough |
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| 1948/1949 | F.A. Cup | 3rd Round | Sat 08 Jan | Brentford | 3 - 2 | Middlesbrough |
| after extra time, 90 minutes ?-? |
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| 1947/1948 | F.A. Cup | 5th Round | Sat 07 Feb | Middlesbrough | 1 - 2 | Derby County |
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| 1946/1947 | F.A. Cup | 6th Round Replay | Tue 04 Mar | Burnley | 1 - 0 | Middlesbrough |
| after extra time, 90 minutes 0-0 |
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| 1945/1946 | F.A. Cup | 5th Round | Wed 13 Feb | Middlesbrough | 1 - 1 | Bolton Wdrs. |
| Bolton Wanderers won 2-1 on aggregate |
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| 1938/1939 | F.A. Cup | 4th Round | Sat 21 Jan | Middlesbrough | 0 - 2 | Sunderland |
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| 1937/1938 | F.A. Cup | 5th Round | Sat 12 Feb | York City | 1 - 0 | Middlesbrough |
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| 1936/1937 | F.A. Cup | 3rd Round | Sat 16 Jan | Wolves | 6 - 1 | Middlesbrough |
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| 1935/1936 | F.A. Cup | 6th Round | Sat 29 Feb | Grimsby Town | 3 - 1 | Middlesbrough |
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| 1934/1935 | F.A. Cup | 3rd Round Replay | Thu 17 Jan | Blackburn R. | 1 - 0 | Middlesbrough |
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| 1933/1934 | F.A. Cup | 3rd Round Replay | Wed 17 Jan | Middlesbrough | 1 - 2 | Sunderland |
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| 1932/1933 | F.A. Cup | 5th Round Replay | Wed 22 Feb | Birmingham | 3 - 0 | Middlesbrough |
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| 1931/1932 | F.A. Cup | 3rd Round Replay | Wed 13 Jan | Portsmouth | 3 - 0 | Middlesbrough |
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| 1930/1931 | F.A. Cup | 3rd Round Replay | Mon 19 Jan | Bradford City | 2 - 1 | Middlesbrough |
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| 1929/1930 | F.A. Cup | 5th Round | Sat 15 Feb | Middlesbrough | 0 - 2 | Arsenal |
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| 1928/1929 | F.A. Cup | 4th Round | Sat 26 Jan | West Brom. | 1 - 0 | Middlesbrough |
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| 1927/1928 | F.A. Cup | 5th Round | Sat 18 Feb | Huddersfield | 4 - 0 | Middlesbrough |
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| 1926/1927 | F.A. Cup | 5th Round | Sat 19 Feb | Millwall | 3 - 2 | Middlesbrough |
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| 1925/1926 | F.A. Cup | 4th Round | Sat 30 Jan | Clapton Orient | 4 - 2 | Middlesbrough |
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| 1924/1925 | F.A. Cup | 1st Round | Sat 10 Jan | Bradford P.A. | 1 - 0 | Middlesbrough |
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| 1923/1924 | F.A. Cup | 1st Round | Sat 12 Jan | Middlesbrough | 0 - 1 | Watford |
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| 1922/1923 | F.A. Cup | 2nd Round Replay | Thu 08 Feb | Sheff. Utd. | 3 - 0 | Middlesbrough |
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| 1921/1922 | F.A. Cup | 1st Round | Sat 07 Jan | Hull City | 5 - 0 | Middlesbrough |
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| 1920/1921 | F.A. Cup | 1st Round | Sat 08 Jan | Derby County | 2 - 0 | Middlesbrough |
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| 1919/1920 | F.A. Cup | 2nd Round | Sat 31 Jan | Notts. County | 1 - 0 | Middlesbrough |
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| 1914/1915 | F.A. Cup | 2nd Round | Sat 30 Jan | Bradford City | 1 - 0 | Middlesbrough |
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| 1913/1914 | F.A. Cup | 1st Round | Sat 10 Jan | Blackburn R. | 3 - 0 | Middlesbrough |
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| 1912/1913 | F.A. Cup | 3rd Round | Sat 22 Feb | Burnley | 3 - 1 | Middlesbrough |
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| 1911/1912 | F.A. Cup | 2nd Round Replay | Thu 08 Feb | West Ham Utd. | 2 - 1 | Middlesbrough |
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| 1910/1911 | F.A. Cup | 3rd Round | Sat 25 Feb | Middlesbrough | 0 - 3 | Blackburn R. |
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| 1909/1910 | F.A. Cup | 1st Round Replay | Wed 19 Jan | Everton | 5 - 3 | Middlesbrough |
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| 1908/1909 | F.A. Cup | 1st Round | Sat 16 Jan | Preston N.E. | 1 - 0 | Middlesbrough |
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| 1907/1908 | F.A. Cup | 1st Round | Sat 11 Jan | Notts. County | 2 - 0 | Middlesbrough |
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| 1906/1907 | F.A. Cup | 2nd Round | Sat 02 Feb | Brentford | 1 - 0 | Middlesbrough |
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| 1905/1906 | F.A. Cup | 3rd Round | Sat 24 Feb | Southampton | 6 - 1 | Middlesbrough |
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| 1904/1905 | F.A. Cup | 1st Round Replay | Thu 09 Feb | Tottenham H. | 1 - 0 | Middlesbrough |
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| 1903/1904 | F.A. Cup | 3rd Round Replay | Wed 09 Mar | Middlesbrough | 1 - 3 | Man. City |
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| 1901/1902 | F.A. Cup | 1st Round Replay | Wed 29 Jan | Bristol Rvs. | 1 - 0 | Middlesbrough |
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| 1900/1901 | F.A. Cup | 3rd Round | Sat 23 Mar | Middlesbrough | 0 - 1 | West Brom. |
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| 1894/1895 | F.A. Cup | 2nd Round | Sat 16 Feb | The Wednesday | 6 - 1 | Middlesbrough |
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| 1893/1894 | F.A. Cup | 1st Round | Sat 27 Jan | Newton Heath | 4 - 0 | Middlesbrough |
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| 1892/1893 | F.A. Cup | 2nd Round | Sat 04 Feb | Wolves | 2 - 1 | |
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