| Season | Competition |
Round Reached | Date |
Home | |
Away |
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| 2007/2008 | F.A. Cup | Semi Final | Sun 06 Apr | Barnsley | 0 - 1 | Cardiff City |
| played at Wembley |
| League Cup | 2nd Round | Wed 29 Aug | Newcastle Utd. | 2 - 0 | Barnsley |
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| 2006/2007 | F.A. Cup | 3rd Round Replay | Tue 16 Jan | Barnsley | 0 - 2 | Southend Utd. |
| League Cup | 2nd Round | Tue 19 Sep | Barnsley | 1 - 2 | Milton Keynes |
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| 2005/2006 | F.A. Cup | 3rd Round Replay | Tue 17 Jan | Walsall | 2 - 0 | Barnsley |
| League Cup | 2nd Round | Tue 20 Sep | Burnley | 3 - 0 | Barnsley |
| (Associate Members) | Northern Section 1st Round | Tue 18 Oct | Barnsley | 2 - 5 | Doncaster Rvs. |
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| 2004/2005 | F.A. Cup | 1st Round | Sat 13 Nov | Northampton | 1 - 0 | Barnsley |
| League Cup | 2nd Round | Tue 21 Sep | Man. City | 7 - 1 | Barnsley |
| (Associate Members) | Northern Section 1st Round | Tue 28 Sep | Port Vale | 1 - 0 | Barnsley |
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| 2003/2004 | F.A. Cup | 3rd Round Replay | Tue 13 Jan | Scunthorpe U. | 2 - 0 | Barnsley |
| League Cup | 1st Round | Tue 12 Aug | Barnsley | 1 - 2 | Blackpool |
| (Associate Members) | Northern Section 2nd Round | Wed 12 Nov | Sheff. Wed. | 1 - 0 | Barnsley |
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| 2002/2003 | F.A. Cup | 1st Round | Sat 16 Nov | Barnsley | 1 - 4 | Blackpool |
| League Cup | 1st Round | Wed 11 Sep | Macclesfield | 4 - 1 | Barnsley |
| after extra time, 90 minutes 1-1 |
| (Associate Members) | Northern Section 2nd Round | Tue 12 Nov | Bury | 1 - 0 | Barnsley |
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| 2001/2002 | F.A. Cup | 3rd Round Replay | Wed 16 Jan | Blackburn R. | 3 - 1 | Barnsley |
| League Cup | 3rd Round | Tue 09 Oct | Barnsley | 0 - 1 | Newcastle Utd. |
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| 2000/2001 | F.A. Cup | 3rd Round | Sat 06 Jan | Leeds Utd. | 1 - 0 | Barnsley |
| League Cup | 3rd Round | Wed 01 Nov | Stoke City | 3 - 2 | Barnsley |
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| 1999/2000 | F.A. Cup | 3rd Round | Sat 11 Dec | Wimbledon | 1 - 0 | Barnsley |
| League Cup | 4th Round | Tue 30 Nov | Tranmere Rvs. | 4 - 0 | Barnsley |
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| 1998/1999 | F.A. Cup | 6th Round | Tue 16 Mar | Barnsley | 0 - 1 | Tottenham H. |
| League Cup | 4th Round | Tue 10 Nov | Luton Town | 1 - 0 | Barnsley |
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| 1997/1998 | F.A. Cup | 6th Round | Sun 08 Mar | Newcastle Utd. | 3 - 1 | Barnsley |
| League Cup | 3rd Round | Tue 14 Oct | Barnsley | 1 - 2 | Southampton |
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| 1996/1997 | F.A. Cup | 4th Round | Sat 25 Jan | Q.P.R. | 3 - 2 | Barnsley |
| League Cup | 2nd Round | Tue 24 Sep | Gillingham | 1 - 0 | Barnsley |
| Gillingham won 2-1 on aggregate |
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| 1995/1996 | F.A. Cup | 3rd Round Replay | Tue 23 Jan | Oldham Ath. | 2 - 1 | Barnsley |
| League Cup | 3rd Round | Tue 24 Oct | Barnsley | 0 - 3 | Arsenal |
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| 1994/1995 | F.A. Cup | 3rd Round | Sat 07 Jan | Barnsley | 0 - 2 | Aston Villa |
| League Cup | 2nd Round | Wed 05 Oct | Barnsley | 0 - 1 | Newcastle Utd. |
| Newcastle United won 3-1 on aggregate |
|
| 1993/1994 | F.A. Cup | 5th Round | Sat 19 Feb | Oldham Ath. | 1 - 0 | Barnsley |
| League Cup | 2nd Round | Tue 05 Oct | Peterborough | 3 - 1 | Barnsley |
| Peterborough United won 4-2 on aggregate |
|
| 1992/1993 | F.A. Cup | 5th Round | Sat 13 Feb | Man. City | 2 - 0 | Barnsley |
| League Cup | 1st Round | Tue 25 Aug | Barnsley | 1 - 1 | Grimsby Town |
| after extra time, 90 minutes 1-1, aggregate 2-2, Grimsby Town won 5-3 on penalties |
|
| 1991/1992 | F.A. Cup | 3rd Round | Sat 04 Jan | Norwich City | 1 - 0 | Barnsley |
| League Cup | 3rd Round | Tue 29 Oct | Middlesbrough | 1 - 0 | Barnsley |
| (Full Members) | Northern Section 1st Round | Wed 02 Oct | Leicester City | 4 - 3 | Barnsley |
| after extra time, 90 minutes 3-3 |
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| 1990/1991 | F.A. Cup | 3rd Round Replay | Wed 09 Jan | Leeds Utd. | 4 - 0 | Barnsley |
| League Cup | 2nd Round | Tue 09 Oct | Barnsley | 0 - 1 | Aston Villa |
| Aston Villa won 2-0 on aggregate |
| (Full Members) | Northern Section Semi-Final | Wed 13 Mar | Barnsley | 0 - 1 | Everton |
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| 1989/1990 | F.A. Cup | 5th Round 2nd Replay | Mon 05 Mar | Barnsley | 0 - 1 | Sheff. Utd. |
| after extra time, 90 minutes 0-0 |
| League Cup | 2nd Round | Tue 03 Oct | Blackpool | 1 - 1 | Barnsley |
| after extra time, 90 minutes 1-1, aggregate 2-2, Blackpool won 5-4 on penalties |
| (Full Members) | Northern Section 2nd Round | Tue 28 Nov | Barnsley | 1 - 2 | Leeds Utd. |
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| 1988/1989 | F.A. Cup | 5th Round | Sat 18 Feb | Barnsley | 0 - 1 | Everton |
| League Cup | 2nd Round | Wed 12 Oct | Wimbledon | 0 - 1 | Barnsley |
| Wimbledon won 2-1 on aggregate |
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| 1987/1988 | F.A. Cup | 4th Round | Sat 30 Jan | Barnsley | 0 - 2 | Birmingham C. |
| League Cup | 3rd Round | Tue 27 Oct | Barnsley | 1 - 2 | Sheff. Wed. |
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| 1986/1987 | F.A. Cup | 5th Round | Sat 21 Feb | Arsenal | 2 - 0 | Barnsley |
| League Cup | 2nd Round | Wed 08 Oct | Tottenham H. | 5 - 3 | Barnsley |
| Tottenham Hotspur won 8-5 on aggregate |
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| 1985/1986 | F.A. Cup | 3rd Round | Mon 13 Jan | Bury | 2 - 0 | Barnsley |
| League Cup | 2nd Round | Tue 08 Oct | Barnsley | 1 - 1 | Newcastle Utd. |
| aggregate 1-1, Newcastle United won on away goals rule |
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| 1984/1985 | F.A. Cup | 6th Round | Sun 10 Mar | Barnsley | 0 - 4 | Liverpool |
| League Cup | 2nd Round | Tue 09 Oct | Barnsley | 1 - 1 | Grimsby Town |
| Grimsby Town won 4-1 on aggregate |
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| 1983/1984 | F.A. Cup | 3rd Round | Sat 07 Jan | Sheff. Wed. | 1 - 0 | Barnsley |
| League Cup | 2nd Round | Tue 25 Oct | Barnsley | 0 - 2 | Walsall |
| Walsall won 3-0 on aggregate |
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| 1982/1983 | F.A. Cup | 4th Round | Sat 29 Jan | Cambridge U. | 1 - 0 | Barnsley |
| League Cup | 4th Round | Tue 30 Nov | Sheff. Wed. | 1 - 0 | Barnsley |
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| 1981/1982 | F.A. Cup | 3rd Round | Tue 05 Jan | Barnsley | 0 - 2 | Blackpool |
| League Cup | Quarter Final Replay | Tue 19 Jan | Barnsley | 1 - 3 | Liverpool |
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| 1980/1981 | F.A. Cup | 5th Round | Sat 14 Feb | Middlesbrough | 2 - 1 | Barnsley |
| League Cup | 4th Round | Tue 28 Oct | West Ham Utd. | 2 - 1 | Barnsley |
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| 1979/1980 | F.A. Cup | 2nd Round | Tue 18 Dec | Chester | 1 - 0 | Barnsley |
| League Cup | 2nd Round | Tue 04 Sep | Barnsley | 0 - 2 | West Ham Utd. |
| West Ham United won 5-1 on aggregate |
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| 1978/1979 | F.A. Cup | 2nd Round Replay | Tue 09 Jan | Rotherham U. | 2 - 1 | Barnsley |
| League Cup | 1st Round | Wed 16 Aug | Chesterfield | 0 - 0 | Barnsley |
| Chesterfield won 2-1 on aggregate |
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| 1977/1978 | F.A. Cup | 2nd Round | Sat 17 Dec | Grimsby Town | 2 - 0 | Barnsley |
| League Cup | 1st Round Replay | Tue 23 Aug | Barnsley | 0 - 2 | Chesterfield |
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| 1976/1977 | F.A. Cup | 2nd Round | Sat 11 Dec | Port Vale | 3 - 0 | Barnsley |
| League Cup | 2nd Round | Wed 01 Sep | West Ham Utd. | 3 - 0 | Barnsley |
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| 1975/1976 | F.A. Cup | 1st Round | Sat 22 Nov | Marine | 3 - 1 | Barnsley |
| League Cup | 1st Round | Wed 27 Aug | Barnsley | 1 - 1 | Huddersfield |
| Huddersfield Town won 3-2 on aggregate |
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| 1974/1975 | F.A. Cup | 1st Round | Sat 23 Nov | Barnsley | 1 - 2 | Halifax Town |
| League Cup | 1st Round | Tue 20 Aug | Barnsley | 0 - 1 | Halifax Town |
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| 1973/1974 | F.A. Cup | 2nd Round Replay | Wed 19 Dec | Bradford City | 2 - 1 | Barnsley |
| League Cup | 1st Round Replay | Tue 04 Sep | Barnsley | 0 - 1 | Halifax Town |
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| 1972/1973 | F.A. Cup | 1st Round | Tue 21 Nov | Halifax Town | 2 - 1 | Barnsley |
| League Cup | 1st Round Replay | Tue 22 Aug | Grimsby Town | 2 - 0 | Barnsley |
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| 1971/1972 | F.A. Cup | 2nd Round Replay | Tue 14 Dec | Chesterfield | 1 - 0 | Barnsley |
| League Cup | 2nd Round | Wed 08 Sep | Arsenal | 1 - 0 | Barnsley |
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| 1970/1971 | F.A. Cup | 2nd Round 2nd Replay | Mon 21 Dec | Barnsley | 0 - 2 | Rhyl |
| played at neutral ground |
| League Cup | 1st Round | Wed 19 Aug | Barnsley | 0 - 1 | Rotherham U. |
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| 1969/1970 | F.A. Cup | 3rd Round | Sat 03 Jan | Mansfield Town | 3 - 2 | Barnsley |
| League Cup | 1st Round | Wed 13 Aug | Barnsley | 0 - 1 | Halifax Town |
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| 1968/1969 | F.A. Cup | 3rd Round Replay | Wed 08 Jan | Leicester City | 2 - 1 | Barnsley |
| League Cup | 2nd Round Replay | Mon 09 Sep | Millwall | 3 - 1 | Barnsley |
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| 1967/1968 | F.A. Cup | 1st Round | Sat 09 Dec | Chesterfield | 2 - 0 | Barnsley |
| League Cup | 1st Round | Tue 22 Aug | Middlesbrough | 4 - 1 | Barnsley |
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| 1966/1967 | F.A. Cup | 3rd Round Replay | Tue 31 Jan | Cardiff City | 2 - 1 | Barnsley |
| League Cup | 1st Round | Wed 24 Aug | Barnsley | 1 - 2 | Grimsby Town |
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| 1965/1966 | F.A. Cup | 2nd Round Replay | Wed 08 Dec | Grimsby Town | 2 - 0 | Barnsley |
| after extra time, 90 minutes 0-0 |
| League Cup | 1st Round Replay | Tue 07 Sep | Barnsley | 1 - 2 | Doncaster Rvs. |
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| 1964/1965 | F.A. Cup | 2nd Round | Sat 05 Dec | Barnsley | 2 - 5 | Chester |
| League Cup | 2nd Round | Wed 23 Sep | Leyton Orient | 3 - 0 | Barnsley |
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| 1963/1964 | F.A. Cup | 5th Round | Sat 15 Feb | Barnsley | 0 - 4 | Man. Utd. |
| League Cup | 2nd Round | Wed 25 Sep | Aston Villa | 3 - 1 | Barnsley |
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| 1962/1963 | F.A. Cup | 3rd Round | Tue 15 Jan | Barnsley | 0 - 3 | Everton |
| League Cup | 3rd Round | Tue 16 Oct | Barnsley | 1 - 2 | Luton Town |
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| 1961/1962 | F.A. Cup | 2nd Round | Sat 25 Nov | Barnsley | 1 - 2 | Carlisle Utd. |
| League Cup | 2nd Round | Mon 09 Oct | Barnsley | 1 - 3 | Workington |
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| 1960/1961 | F.A. Cup | 6th Round Replay | Wed 08 Mar | Barnsley | 1 - 2 | Leicester City |
| League Cup | 2nd Round | Wed 19 Oct | Derby County | 3 - 0 | Barnsley |
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| 1959/1960 | F.A. Cup | 1st Round Replay | Wed 18 Nov | Bradford City | 2 - 1 | Barnsley |
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| 1958/1959 | F.A. Cup | 3rd Round | Sat 10 Jan | Brentford | 2 - 0 | Barnsley |
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| 1957/1958 | F.A. Cup | 3rd Round Replay | Wed 08 Jan | Barnsley | 0 - 2 | Hull City |
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| 1956/1957 | F.A. Cup | 5th Round | Sat 16 Feb | Barnsley | 1 - 2 | Nottm. Forest |
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| 1955/1956 | F.A. Cup | 4th Round | Sat 28 Jan | Barnsley | 0 - 1 | Blackburn R. |
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| 1954/1955 | F.A. Cup | 2nd Round Replay | Thu 16 Dec | Barnsley | 0 - 1 | Gateshead |
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| 1953/1954 | F.A. Cup | 2nd Round | Sat 12 Dec | Norwich City | 2 - 1 | Barnsley |
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| 1952/1953 | F.A. Cup | 4th Round | Sat 31 Jan | Plymouth Arg. | 1 - 0 | Barnsley |
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| 1951/1952 | F.A. Cup | 4th Round | Sat 02 Feb | Arsenal | 4 - 0 | Barnsley |
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| 1950/1951 | F.A. Cup | 3rd Round | Sat 06 Jan | Northampton | 3 - 1 | Barnsley |
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| 1949/1950 | F.A. Cup | 3rd Round | Sat 07 Jan | Stockport Co. | 4 - 2 | Barnsley |
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| 1948/1949 | F.A. Cup | 3rd Round | Sat 08 Jan | Barnsley | 0 - 1 | Blackpool |
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| 1947/1948 | F.A. Cup | 3rd Round | Sat 10 Jan | Man. City | 2 - 1 | Barnsley |
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| 1946/1947 | F.A. Cup | 4th Round | Sat 25 Jan | Preston N.E. | 6 - 0 | Barnsley |
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| 1945/1946 | F.A. Cup | 5th Round | Wed 13 Feb | Bradford P.A. | 1 - 1 | Barnsley |
| Bradford Park Avenue won 2-1 on aggregate |
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| 1938/1939 | F.A. Cup | 3rd Round | Sat 07 Jan | Barnsley | 1 - 2 | Stockport Co. |
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| 1937/1938 | F.A. Cup | 4th Round Replay | Wed 26 Jan | Man. Utd. | 1 - 0 | Barnsley |
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| 1936/1937 | F.A. Cup | 3rd Round | Sat 16 Jan | Walsall | 3 - 1 | Barnsley |
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| 1935/1936 | F.A. Cup | 6th Round | Sat 29 Feb | Arsenal | 4 - 1 | Barnsley |
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| 1934/1935 | F.A. Cup | 3rd Round Replay | Wed 16 Jan | Barnsley | 0 - 1 | Preston N.E. |
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| 1933/1934 | F.A. Cup | 1st Round | Sat 25 Nov | Halifax Town | 3 - 2 | Barnsley |
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| 1932/1933 | F.A. Cup | 3rd Round Replay | Wed 18 Jan | Luton Town | 2 - 0 | Barnsley |
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| 1931/1932 | F.A. Cup | 3rd Round Replay | Tue 12 Jan | Southport | 4 - 1 | Barnsley |
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| 1930/1931 | F.A. Cup | 5th Round | Sat 14 Feb | Barnsley | 1 - 3 | Wolves |
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| 1929/1930 | F.A. Cup | 3rd Round | Sat 11 Jan | Barnsley | 0 - 1 | Bradford P.A. |
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| 1928/1929 | F.A. Cup | 3rd Round | Sat 12 Jan | Blackburn R. | 1 - 0 | Barnsley |
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| 1927/1928 | F.A. Cup | 3rd Round | Sat 14 Jan | Port Vale | 3 - 0 | Barnsley |
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| 1926/1927 | F.A. Cup | 4th Round | Sat 29 Jan | Barnsley | 1 - 3 | Swansea Town |
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| 1925/1926 | F.A. Cup | 1st Round | Sat 28 Nov | Northampton | 3 - 1 | Barnsley |
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| 1924/1925 | F.A. Cup | 2nd Round | Sat 31 Jan | Barnsley | 0 - 3 | Bradford City |
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| 1923/1924 | F.A. Cup | 1st Round Replay | Wed 16 Jan | Brighton & HA | 1 - 0 | Barnsley |
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| 1922/1923 | F.A. Cup | 2nd Round | Sat 03 Feb | The Wednesday | 2 - 1 | Barnsley |
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| 1921/1922 | F.A. Cup | 3rd Round Replay | Wed 22 Feb | Preston N.E. | 3 - 0 | Barnsley |
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| 1920/1921 | F.A. Cup | 1st Round | Sat 08 Jan | Bradford City | 3 - 1 | Barnsley |
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| 1919/1920 | F.A. Cup | 2nd Round | Sat 31 Jan | Plymouth Arg. | 4 - 1 | Barnsley |
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| 1914/1915 | F.A. Cup | 1st Round | Sat 09 Jan | Everton | 3 - 0 | Barnsley |
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| 1913/1914 | F.A. Cup | 1st Round Replay | Thu 15 Jan | Barnsley | 0 - 1 | Liverpool |
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| 1912/1913 | F.A. Cup | 2nd Round | Sat 01 Feb | Barnsley | 2 - 3 | Blackburn R. |
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| 1911/1912 | F.A. Cup | Final Replay | Wed 24 Apr | Barnsley | 1 - 0 | West Brom. |
| played at Bramall Lane |
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| 1910/1911 | F.A. Cup | 2nd Round | Sat 04 Feb | Burnley | 2 - 0 | Barnsley |
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| 1909/1910 | F.A. Cup | Final Replay | Thu 28 Apr | Newcastle Utd. | 2 - 0 | Barnsley |
| played at Goodison Park |
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| 1908/1909 | F.A. Cup | 1st Round | Sat 16 Jan | Everton | 3 - 1 | Barnsley |
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| 1907/1908 | F.A. Cup | 1st Round | Sat 11 Jan | Plymouth Arg. | 1 - 0 | Barnsley |
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| 1906/1907 | F.A. Cup | 4th Round | Sat 09 Mar | Barnsley | 1 - 2 | Woolwich Arsenal |
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| 1905/1906 | F.A. Cup | 2nd Round | Sat 03 Feb | Liverpool | 1 - 0 | Barnsley |
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| 1902/1903 | F.A. Cup | 2nd Round | Sat 21 Feb | Aston Villa | 4 - 1 | Barnsley |
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| 1896/1897 | F.A. Cup | 1st Round | Sat 30 Jan | Derby County | 8 - 1 | Barnsley |
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| 1894/1895 | F.A. Cup | 1st Round | Mon 11 Feb | Liverpool | 4 - 0 | Barnsley |
| replayed after initial void game 02/02 (1-2) |
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