| Season | Competition |
Round Reached | Date |
Home | |
Away |
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| 2008/2009 | League Cup | 2nd Round | Tue 26 Aug | Burnley | 3 - 0 | Oldham Ath. |
| (Associate Members) | Northern Section 1st Round | Tue 02 Sep | Oldham Ath. | v | Morecambe |
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| 2007/2008 | F.A. Cup | 4th Round | Sat 26 Jan | Oldham Ath. | 0 - 1 | Huddersfield |
| League Cup | 2nd Round | Tue 28 Aug | Burnley | 3 - 0 | Oldham Ath. |
| (Associate Members) | Northern Section 2nd Round | Tue 23 Oct | Doncaster Rvs. | 3 - 0 | Oldham Ath. |
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| 2006/2007 | F.A. Cup | 3rd Round Replay | Tue 16 Jan | Oldham Ath. | 0 - 2 | Wolves |
| League Cup | 1st Round | Tue 22 Aug | Rotherham U. | 3 - 1 | Oldham Ath. |
| (Associate Members) | Northern Section 2nd Round | Wed 01 Nov | Oldham Ath. | 0 - 1 | Chesterfield |
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| 2005/2006 | F.A. Cup | 2nd Round Replay | Tue 13 Dec | Brentford | 1 - 0 | Oldham Ath. |
| League Cup | 1st Round | Tue 23 Aug | Leeds Utd. | 2 - 0 | Oldham Ath. |
| (Associate Members) | Northern Section 1st Round | Tue 18 Oct | Oldham Ath. | 1 - 1 | Carlisle Utd. |
| after extra time, 90 minutes 1-1, Carlisle United won 6-5 on penalties |
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| 2004/2005 | F.A. Cup | 4th Round | Sun 30 Jan | Oldham Ath. | 0 - 1 | Bolton Wdrs. |
| League Cup | 2nd Round | Wed 22 Sep | Oldham Ath. | 0 - 6 | Tottenham H. |
| (Associate Members) | Northern Section Final | Tue 08 Mar | Wrexham | 1 - 0 | Oldham Ath. |
| Wrexham won 6-3 on aggregate |
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| 2003/2004 | F.A. Cup | 2nd Round | Sat 06 Dec | Oldham Ath. | 2 - 5 | Blackpool |
| League Cup | 1st Round | Tue 12 Aug | Scunthorpe U. | 2 - 1 | Oldham Ath. |
| (Associate Members) | Northern Section 2nd Round | Mon 03 Nov | Bury | 2 - 1 | Oldham Ath. |
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| 2002/2003 | F.A. Cup | 2nd Round | Sat 07 Dec | Oldham Ath. | 1 - 2 | Cheltenham T. |
| League Cup | 4th Round | Tue 03 Dec | Crystal Palace | 2 - 0 | Oldham Ath. |
| (Associate Members) | Northern Section 1st Round | Tue 22 Oct | Oldham Ath. | 3 - 4 | Carlisle Utd. |
| after extra time, 90 minutes 3-3, Carlisle United won on golden goal rule |
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| 2001/2002 | F.A. Cup | 3rd Round | Sun 06 Jan | Cheltenham T. | 2 - 1 | Oldham Ath. |
| League Cup | 2nd Round | Wed 12 Sep | Blackburn R. | 2 - 0 | Oldham Ath. |
| (Associate Members) | Northern Section Semi-Final | Wed 09 Jan | Oldham Ath. | 2 - 5 | Blackpool |
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| 2000/2001 | F.A. Cup | 2nd Round Replay | Tue 19 Dec | Oldham Ath. | 0 - 1 | Peterborough |
| League Cup | 2nd Round | Wed 27 Sep | Sheff. Wed. | 5 - 1 | Oldham Ath. |
| (Associate Members) | Northern Section 1st Round | Tue 09 Jan | Oldham Ath. | 2 - 3 | Wigan Ath. |
| after extra time, 90 minutes 2-2, Wigan Athletic won on golden goal rule |
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| 1999/2000 | F.A. Cup | 3rd Round | Sat 11 Dec | Preston N.E. | 2 - 1 | Oldham Ath. |
| League Cup | 1st Round | Tue 24 Aug | Oldham Ath. | 1 - 1 | Stockport Co. |
| Stockport County won 3-1 on aggregate |
| (Associate Members) | Northern Section 2nd Round | Tue 18 Jan | Oldham Ath. | 0 - 1 | Stoke City |
| after extra time, 90 minutes 0-0, Stoke City won on golden goal rule |
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| 1998/1999 | F.A. Cup | 3rd Round | Sat 02 Jan | Oldham Ath. | 0 - 2 | Chelsea |
| League Cup | 1st Round | Tue 18 Aug | Crewe Alex. | 2 - 0 | Oldham Ath. |
| Crewe Alexandra won 4-3 on aggregate |
| (Associate Members) | Northern Section 1st Round | Tue 08 Dec | Oldham Ath. | 0 - 1 | Darlington |
| after extra time, 90 minutes 0-0, Darlington won on golden goal rule |
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| 1997/1998 | F.A. Cup | 3rd Round | Sat 03 Jan | Cardiff City | 1 - 0 | Oldham Ath. |
| League Cup | 1st Round | Tue 26 Aug | Grimsby Town | 5 - 0 | Oldham Ath. |
| Grimsby Town won 5-1 on aggregate |
| (Associate Members) | Northern Section 1st Round | Tue 09 Dec | Carlisle Utd. | 1 - 0 | Oldham Ath. |
| after extra time, 90 minutes 0-0, Carlisle United won on golden goal rule |
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| 1996/1997 | F.A. Cup | 3rd Round | Tue 14 Jan | Barnsley | 2 - 0 | Oldham Ath. |
| League Cup | 3rd Round | Wed 23 Oct | Newcastle Utd. | 1 - 0 | Oldham Ath. |
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| 1995/1996 | F.A. Cup | 4th Round | Mon 12 Feb | Swindon Town | 1 - 0 | Oldham Ath. |
| League Cup | 2nd Round | Wed 04 Oct | Oldham Ath. | 1 - 3 | Tranmere Rvs. |
| Tranmere Rovers won 4-1 on aggregate |
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| 1994/1995 | F.A. Cup | 4th Round | Sat 28 Jan | Leeds Utd. | 3 - 2 | Oldham Ath. |
| League Cup | 3rd Round Replay | Wed 09 Nov | Arsenal | 2 - 0 | Oldham Ath. |
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| 1993/1994 | F.A. Cup | Semi Final Replay | Wed 13 Apr | Man. Utd. | 4 - 1 | Oldham Ath. |
| played at Maine Road |
| League Cup | 4th Round | Tue 30 Nov | Tranmere Rvs. | 3 - 0 | Oldham Ath. |
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| 1992/1993 | F.A. Cup | 3rd Round Replay | Tue 12 Jan | Tranmere Rvs. | 3 - 0 | Oldham Ath. |
| League Cup | 4th Round | Tue 01 Dec | Cambridge U. | 1 - 0 | Oldham Ath. |
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| 1991/1992 | F.A. Cup | 3rd Round Replay | Wed 15 Jan | Leyton Orient | 4 - 2 | Oldham Ath. |
| after extra time, 90 minutes ?-? |
| League Cup | 4th Round | Wed 04 Dec | Man. Utd. | 2 - 0 | Oldham Ath. |
| (Full Members) | Northern Section 2nd Round | Tue 01 Oct | Everton | 3 - 2 | Oldham Ath. |
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| 1990/1991 | F.A. Cup | 4th Round | Sat 26 Jan | Notts. County | 2 - 0 | Oldham Ath. |
| League Cup | 3rd Round | Wed 31 Oct | Leeds Utd. | 2 - 0 | Oldham Ath. |
| (Full Members) | Northern Section 2nd Round | Tue 11 Dec | Sheff. Utd. | 7 - 2 | Oldham Ath. |
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| 1989/1990 | F.A. Cup | Semi Final Replay | Wed 11 Apr | Man. Utd. | 2 - 1 | Oldham Ath. |
| after extra time, 90 minutes 1-1; played at Maine Road |
| League Cup | Final | Sun 29 Apr | Nottm. Forest | 1 - 0 | Oldham Ath. |
| played at Wembley |
| (Full Members) | Northern Section 2nd Round | Tue 28 Nov | Newcastle Utd. | 2 - 0 | Oldham Ath. |
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| 1988/1989 | F.A. Cup | 3rd Round | Sat 07 Jan | Charlton Ath. | 2 - 1 | Oldham Ath. |
| League Cup | 3rd Round Replay | Tue 29 Nov | Oldham Ath. | 0 - 2 | Everton |
| (Full Members) | 1st Round | Wed 14 Dec | Middlesbrough | 1 - 0 | Oldham Ath. |
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| 1987/1988 | F.A. Cup | 3rd Round | Sat 09 Jan | Oldham Ath. | 2 - 4 | Tottenham H. |
| League Cup | 4th Round | Tue 17 Nov | Everton | 2 - 1 | Oldham Ath. |
| (Full Members) | 1st Round | Tue 10 Nov | Oldham Ath. | 0 - 3 | West Brom. |
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| 1986/1987 | F.A. Cup | 3rd Round Replay | Mon 19 Jan | Bradford City | 5 - 1 | Oldham Ath. |
| League Cup | 3rd Round | Tue 28 Oct | Coventry City | 2 - 1 | Oldham Ath. |
| (Full Members) | 1st Round | Tue 16 Sep | Oldham Ath. | 0 - 1 | Derby County |
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| 1985/1986 | F.A. Cup | 3rd Round | Mon 06 Jan | Oldham Ath. | 1 - 2 | Orient |
| League Cup | 2nd Round | Wed 09 Oct | Oldham Ath. | 2 - 5 | Liverpool |
| Liverpool won 8-2 on aggregate |
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| 1984/1985 | F.A. Cup | 4th Round | Sat 26 Jan | Sheff. Wed. | 5 - 1 | Oldham Ath. |
| League Cup | 1st Round | Tue 04 Sep | Oldham Ath. | 4 - 4 | Bolton Wdrs. |
| Bolton Wanderers won 6-5 on aggregate |
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| 1983/1984 | F.A. Cup | 3rd Round | Sat 07 Jan | Shrewsbury Tn. | 3 - 0 | Oldham Ath. |
| League Cup | 3rd Round | Tue 08 Nov | Wimbledon | 3 - 1 | Oldham Ath. |
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| 1982/1983 | F.A. Cup | 3rd Round | Sat 08 Jan | Oldham Ath. | 0 - 2 | Fulham |
| League Cup | 2nd Round | Tue 26 Oct | Oldham Ath. | 1 - 0 | Gillingham |
| Gillingham won 2-1 on aggregate |
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| 1981/1982 | F.A. Cup | 3rd Round | Tue 05 Jan | Gillingham | 2 - 1 | Oldham Ath. |
| League Cup | 3rd Round Replay | Tue 17 Nov | Fulham | 3 - 0 | Oldham Ath. |
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| 1980/1981 | F.A. Cup | 3rd Round Replay | Tue 06 Jan | Oldham Ath. | 0 - 1 | Wimbledon |
| League Cup | 2nd Round | Tue 02 Sep | Portsmouth | 1 - 0 | Oldham Ath. |
| aggregate 3-3, Portsmouth won on away goals rule |
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| 1979/1980 | F.A. Cup | 3rd Round | Sat 05 Jan | Oldham Ath. | 0 - 1 | Coventry City |
| League Cup | 2nd Round | Tue 04 Sep | Oldham Ath. | 3 - 1 | Northampton |
| Northampton Town won 4-3 on aggregate |
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| 1978/1979 | F.A. Cup | 5th Round | Wed 28 Feb | Oldham Ath. | 0 - 1 | Tottenham H. |
| League Cup | 2nd Round Replay | Wed 06 Sep | Nottm. Forest | 4 - 2 | Oldham Ath. |
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| 1977/1978 | F.A. Cup | 3rd Round Replay | Mon 09 Jan | Oldham Ath. | 1 - 2 | Luton Town |
| League Cup | 3rd Round | Tue 25 Oct | Hull City | 2 - 0 | Oldham Ath. |
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| 1976/1977 | F.A. Cup | 5th Round | Sat 26 Feb | Liverpool | 3 - 1 | Oldham Ath. |
| League Cup | 1st Round | Tue 17 Aug | Oldham Ath. | 1 - 3 | Bradford City |
| Bradford City won 4-2 on aggregate |
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| 1975/1976 | F.A. Cup | 3rd Round | Sat 03 Jan | Sunderland | 2 - 0 | Oldham Ath. |
| League Cup | 2nd Round | Wed 10 Sep | Aston Villa | 2 - 0 | Oldham Ath. |
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| 1974/1975 | F.A. Cup | 3rd Round | Sat 04 Jan | Oldham Ath. | 0 - 3 | Aston Villa |
| League Cup | 1st Round | Tue 20 Aug | Bury | 2 - 0 | Oldham Ath. |
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| 1973/1974 | F.A. Cup | 4th Round | Sat 26 Jan | Oldham Ath. | 1 - 4 | Burnley |
| League Cup | 1st Round Replay | Tue 04 Sep | Oldham Ath. | 2 - 3 | Bury |
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| 1972/1973 | F.A. Cup | 1st Round Replay | Wed 22 Nov | Scarborough | 2 - 1 | Oldham Ath. |
| League Cup | 1st Round | Wed 16 Aug | Bolton Wdrs. | 3 - 0 | Oldham Ath. |
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| 1971/1972 | F.A. Cup | 1st Round | Sat 20 Nov | Chesterfield | 3 - 0 | Oldham Ath. |
| League Cup | 2nd Round | Wed 08 Sep | Torquay Utd. | 2 - 1 | Oldham Ath. |
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| 1970/1971 | F.A. Cup | 1st Round | Sat 21 Nov | Rochdale | 2 - 0 | Oldham Ath. |
| League Cup | 2nd Round | Tue 08 Sep | Oldham Ath. | 2 - 4 | Middlesbrough |
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| 1969/1970 | F.A. Cup | 2nd Round Replay | Tue 09 Dec | Oldham Ath. | 1 - 2 | South Shields |
| League Cup | 1st Round | Wed 13 Aug | Southport | 5 - 1 | Oldham Ath. |
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| 1968/1969 | F.A. Cup | 1st Round | Sat 16 Nov | Wrexham | 4 - 2 | Oldham Ath. |
| League Cup | 1st Round Replay | Wed 21 Aug | Oldham Ath. | 0 - 1 | Preston N.E. |
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| 1967/1968 | F.A. Cup | 1st Round | Sat 09 Dec | Barrow | 2 - 0 | Oldham Ath. |
| League Cup | 1st Round 2nd Replay | Fri 01 Sep | Workington | 2 - 1 | Oldham Ath. |
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| 1966/1967 | F.A. Cup | 3rd Round Replay | Wed 01 Feb | Wolves | 4 - 1 | Oldham Ath. |
| League Cup | 1st Round | Wed 24 Aug | Barrow | 2 - 1 | Oldham Ath. |
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| 1965/1966 | F.A. Cup | 3rd Round Replay | Mon 24 Jan | West Ham Utd. | 2 - 1 | Oldham Ath. |
| League Cup | 2nd Round | Wed 22 Sep | Oldham Ath. | 1 - 2 | Portsmouth |
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| 1964/1965 | F.A. Cup | 3rd Round | Sat 09 Jan | Middlesbrough | 6 - 2 | Oldham Ath. |
| League Cup | 2nd Round | Wed 23 Sep | Grimsby Town | 3 - 1 | Oldham Ath. |
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| 1963/1964 | F.A. Cup | 3rd Round | Sat 04 Jan | Ipswich Town | 6 - 3 | Oldham Ath. |
| League Cup | 1st Round | Wed 04 Sep | Oldham Ath. | 3 - 5 | Workington |
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| 1962/1963 | F.A. Cup | 1st Round | Sat 03 Nov | Oldham Ath. | 2 - 5 | Bradford City |
| League Cup | 2nd Round | Mon 24 Sep | Sunderland | 7 - 1 | Oldham Ath. |
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| 1961/1962 | F.A. Cup | 4th Round | Sat 27 Jan | Oldham Ath. | 1 - 2 | Liverpool |
| League Cup | 1st Round | Tue 12 Sep | Oldham Ath. | 1 - 4 | Charlton Ath. |
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| 1960/1961 | F.A. Cup | 2nd Round Replay | Tue 29 Nov | Oldham Ath. | 0 - 3 | Chesterfield |
| League Cup | 2nd Round | Wed 26 Oct | Norwich City | 6 - 2 | Oldham Ath. |
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| 1959/1960 | F.A. Cup | 2nd Round | Sat 05 Dec | Bury | 2 - 1 | Oldham Ath. |
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| 1958/1959 | F.A. Cup | 3rd Round | Sat 10 Jan | Stoke City | 5 - 1 | Oldham Ath. |
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| 1957/1958 | F.A. Cup | 2nd Round | Sat 07 Dec | Oldham Ath. | 1 - 5 | Workington |
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| 1956/1957 | F.A. Cup | 2nd Round | Sat 08 Dec | Accrington S. | 2 - 1 | Oldham Ath. |
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| 1955/1956 | F.A. Cup | 1st Round | Sat 19 Nov | Bradford City | 3 - 1 | Oldham Ath. |
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| 1954/1955 | F.A. Cup | 2nd Round | Sat 11 Dec | Bournemouth & Boscombe Ath. | 1 - 0 | Oldham Ath. |
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| 1953/1954 | F.A. Cup | 3rd Round Replay | Tue 12 Jan | Oldham Ath. | 0 - 1 | Ipswich Town |
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| 1952/1953 | F.A. Cup | 3rd Round | Wed 14 Jan | Oldham Ath. | 1 - 3 | Birmingham C. |
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| 1951/1952 | F.A. Cup | 2nd Round | Sat 15 Dec | Southend Utd. | 5 - 0 | Oldham Ath. |
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| 1950/1951 | F.A. Cup | 3rd Round | Sat 06 Jan | Man. Utd. | 4 - 1 | Oldham Ath. |
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| 1949/1950 | F.A. Cup | 3rd Round | Sat 07 Jan | Oldham Ath. | 2 - 7 | Newcastle Utd. |
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| 1948/1949 | F.A. Cup | 3rd Round | Sat 08 Jan | Oldham Ath. | 2 - 3 | Cardiff City |
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| 1947/1948 | F.A. Cup | 2nd Round | Sat 13 Dec | Oldham Ath. | 0 - 1 | Mansfield Town |
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| 1946/1947 | F.A. Cup | 2nd Round | Sat 14 Dec | Oldham Ath. | 1 - 2 | Doncaster Rvs. |
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| 1945/1946 | F.A. Cup | 2nd Round | Sat 15 Dec | Accrington S. | 3 - 1 | Oldham Ath. |
| Accrington Stanley won 4-3 on aggregate |
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| 1938/1939 | F.A. Cup | 1st Round Replay | Wed 30 Nov | Crewe Alex. | 1 - 0 | Oldham Ath. |
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| 1937/1938 | F.A. Cup | 1st Round | Sat 27 Nov | Wrexham | 2 - 1 | Oldham Ath. |
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| 1936/1937 | F.A. Cup | 3rd Round | Sat 16 Jan | Exeter City | 3 - 0 | Oldham Ath. |
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| 1935/1936 | F.A. Cup | 2nd Round Replay | Wed 18 Dec | Bristol Rvs. | 4 - 1 | Oldham Ath. |
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| 1934/1935 | F.A. Cup | 3rd Round | Sat 12 Jan | Sheff. Wed. | 3 - 1 | Oldham Ath. |
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| 1933/1934 | F.A. Cup | 4th Round Replay | Wed 31 Jan | Sheff. Wed. | 6 - 1 | Oldham Ath. |
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| 1932/1933 | F.A. Cup | 3rd Round | Sat 14 Jan | Oldham Ath. | 0 - 6 | Tottenham H. |
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| 1931/1932 | F.A. Cup | 3rd Round Replay | Wed 13 Jan | Huddersfield | 6 - 0 | Oldham Ath. |
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| 1930/1931 | F.A. Cup | 3rd Round | Sat 10 Jan | Oldham Ath. | 1 - 3 | Watford |
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| 1929/1930 | F.A. Cup | 4th Round | Sat 25 Jan | Oldham Ath. | 3 - 4 | Sheff. Wed. |
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| 1928/1929 | F.A. Cup | 3rd Round | Sat 12 Jan | Bolton Wdrs. | 2 - 0 | Oldham Ath. |
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| 1927/1928 | F.A. Cup | 4th Round | Sat 28 Jan | Tottenham H. | 3 - 0 | Oldham Ath. |
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| 1926/1927 | F.A. Cup | 3rd Round | Mon 10 Jan | Oldham Ath. | 2 - 4 | Brentford |
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| 1925/1926 | F.A. Cup | 3rd Round Replay | Tue 12 Jan | Oldham Ath. | 0 - 1 | Millwall |
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| 1924/1925 | F.A. Cup | 1st Round | Sat 10 Jan | Blackburn R. | 1 - 0 | Oldham Ath. |
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| 1923/1924 | F.A. Cup | 2nd Round | Sat 02 Feb | Swindon Town | 2 - 0 | Oldham Ath. |
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| 1922/1923 | F.A. Cup | 1st Round | Sat 13 Jan | Oldham Ath. | 0 - 1 | Middlesbrough |
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| 1921/1922 | F.A. Cup | 2nd Round | Sat 28 Jan | Barnsley | 3 - 1 | Oldham Ath. |
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| 1920/1921 | F.A. Cup | 1st Round | Sat 08 Jan | Brighton & HA | 4 - 1 | Oldham Ath. |
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| 1919/1920 | F.A. Cup | 1st Round | Sat 10 Jan | Cardiff City | 2 - 0 | Oldham Ath. |
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| 1914/1915 | F.A. Cup | 4th Round Replay | Sat 13 Mar | Sheff. Utd. | 3 - 0 | Oldham Ath. |
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| 1913/1914 | F.A. Cup | 1st Round Replay | Wed 14 Jan | Brighton & HA | 1 - 0 | Oldham Ath. |
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| 1912/1913 | F.A. Cup | Semi Final | Sat 29 Mar | Aston Villa | 1 - 0 | Oldham Ath. |
| played at Ewood Park |
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| 1911/1912 | F.A. Cup | 3rd Round | Sat 24 Feb | Oldham Ath. | 0 - 2 | Everton |
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| 1910/1911 | F.A. Cup | 2nd Round | Sat 04 Feb | Hull City | 1 - 0 | Oldham Ath. |
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| 1909/1910 | F.A. Cup | 1st Round | Sat 15 Jan | Oldham Ath. | 1 - 2 | Aston Villa |
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| 1908/1909 | F.A. Cup | 1st Round Replay | Wed 20 Jan | Leeds City | 2 - 0 | Oldham Ath. |
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| 1907/1908 | F.A. Cup | 2nd Round Replay | Wed 05 Feb | Everton | 6 - 1 | Oldham Ath. |
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| 1906/1907 | F.A. Cup | 2nd Round | Sat 02 Feb | Oldham Ath. | 0 - 1 | Liverpool |