| Season | Competition |
Round Reached | Date |
Home | |
Away |
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| 2007/2008 | F.A. Cup | 1st Round | Sat 10 Nov | York City | 0 - 1 | Havant & W. |
| Trophy | Semi Final | Sat 15 Mar | York City | 1 - 0 | Torquay Utd. |
| Torquay United won 2-1 on aggregate |
| Shield (Conference Cup) | Northern Section Quarter-Final | Wed 06 Feb | York City | 3 - 3 | Northwich Vic. |
| after extra time, 90 minutes 2-2, Northwich Victoria won 3-2 on penalties |
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| 2006/2007 | F.A. Cup | 1st Round | Sat 11 Nov | York City | 0 - 1 | Bristol City |
| Trophy | 1st Round | Sat 16 Dec | Morecambe | 2 - 1 | York City |
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| 2005/2006 | F.A. Cup | 1st Round | Sat 05 Nov | York City | 0 - 3 | Grays Ath. |
| Trophy | 1st Round | Sat 17 Dec | York City | 1 - 2 | Northwich Vic. |
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| 2004/2005 | F.A. Cup | 4th Qualifying Round | Sat 30 Oct | Carlisle Utd. | 3 - 1 | York City |
| (Associate Members) | Northern Section 1st Round | Wed 29 Sep | York City | 0 - 2 | Blackpool |
| Trophy | 3rd Round | Sat 15 Jan | Burton Albion | 3 - 0 | York City |
| Shield (Conference Cup) | Northern Section 3rd Round | Tue 25 Jan | Accrington S. | 2 - 1 | York City |
| after extra time, 90 minutes 1-1 |
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| 2003/2004 | F.A. Cup | 1st Round | Sun 09 Nov | York City | 1 - 2 | Barnsley |
| League Cup | 1st Round | Tue 12 Aug | Rotherham U. | 2 - 1 | York City |
| (Associate Members) | Northern Section 1st Round | Tue 14 Oct | Halifax Town | 2 - 1 | York City |
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| 2002/2003 | F.A. Cup | 2nd Round | Sat 07 Dec | York City | 1 - 2 | Brentford |
| League Cup | 1st Round | Tue 10 Sep | Sheff. Utd. | 1 - 0 | York City |
| (Associate Members) | Northern Section 1st Round | Tue 22 Oct | Lincoln City | 4 - 3 | York City |
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| 2001/2002 | F.A. Cup | 4th Round | Sat 26 Jan | York City | 0 - 2 | Fulham |
| League Cup | 1st Round | Tue 21 Aug | York City | 2 - 2 | Crewe Alex. |
| after extra time, 90 minutes 1-1, Crewe Alexandra won 6-5 on penalties |
| (Associate Members) | Northern Section 1st Round | Tue 16 Oct | Notts. County | 2 - 0 | York City |
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| 2000/2001 | F.A. Cup | 3rd Round | Sat 06 Jan | Leicester City | 3 - 0 | York City |
| League Cup | 1st Round | Wed 06 Sep | Stoke City | 0 - 0 | York City |
| (Associate Members) | Northern Section 1st Round | Tue 09 Jan | York City | 0 - 4 | Darlington |
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| 1999/2000 | F.A. Cup | 1st Round | Sat 30 Oct | Hereford Utd. | 1 - 0 | York City |
| League Cup | 1st Round | Tue 24 Aug | Wigan Ath. | 2 - 1 | York City |
| Wigan Athletic won 3-1 on aggregate |
| (Associate Members) | Northern Section 1st Round | Tue 07 Dec | York City | 0 - 1 | Hull City |
|
| 1998/1999 | F.A. Cup | 2nd Round | Sat 05 Dec | Wrexham | 2 - 1 | York City |
| League Cup | 1st Round | Tue 18 Aug | Sunderland | 2 - 1 | York City |
| Sunderland won 4-1 on aggregate |
| (Associate Members) | Northern Section 2nd Round | Tue 05 Jan | Halifax Town | 4 - 2 | York City |
|
| 1997/1998 | F.A. Cup | 2nd Round | Sat 06 Dec | Wigan Ath. | 2 - 1 | York City |
| League Cup | 2nd Round | Tue 23 Sep | York City | 1 - 2 | Oxford Utd. |
| Oxford United won 6-2 on aggregate |
| (Associate Members) | Northern Section 2nd Round | Tue 06 Jan | Blackpool | 1 - 1 | York City |
| after extra time, 90 minutes 1-1, Blackpool won 10-9 on penalties |
|
| 1996/1997 | F.A. Cup | 3rd Round | Mon 13 Jan | Hednesford T. | 1 - 0 | York City |
| League Cup | 3rd Round | Tue 22 Oct | York City | 0 - 2 | Leicester City |
| (Associate Members) | Northern Section Quarter-Final | Tue 04 Feb | York City | 0 - 2 | Carlisle Utd. |
|
| 1995/1996 | F.A. Cup | 1st Round | Sun 12 Nov | York City | 0 - 1 | Notts. County |
| League Cup | 3rd Round | Wed 25 Oct | Q.P.R. | 3 - 1 | York City |
| (Associate Members) | Northern Section Semi-Final | Tue 13 Feb | Rotherham U. | 4 - 1 | York City |
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| 1994/1995 | F.A. Cup | 1st Round Replay | Tue 22 Nov | Rotherham U. | 3 - 0 | York City |
| League Cup | 1st Round | Tue 23 Aug | York City | 2 - 2 | Burnley |
| Burnley won 3-2 on aggregate |
| (Associate Members) | Northern Section Preliminary Round Group Seven | Tue 08 Nov | York City | 2 - 2 | Bradford City |
|
| 1993/1994 | F.A. Cup | 1st Round Replay | Tue 30 Nov | York City | 2 - 3 | Burnley |
| League Cup | 1st Round | Tue 24 Aug | York City | 0 - 0 | Rochdale |
| Rochdale won 2-0 on aggregate |
| (Associate Members) | Northern Section 1st Round | Sat 04 Dec | York City | 1 - 1 | Mansfield Town |
| after extra time, 90 minutes 1-1, Mansfield Town won 5-4 on penalties |
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| 1992/1993 | F.A. Cup | 1st Round | Sat 14 Nov | York City | 1 - 3 | Stockport Co. |
| League Cup | 1st Round | Tue 25 Aug | York City | 0 - 0 | Chesterfield |
| Chesterfield won 2-0 on aggregate |
| (Associate Members) | Northern Section Preliminary Round Group One | Tue 08 Dec | York City | 0 - 0 | Hull City |
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| 1991/1992 | F.A. Cup | 2nd Round Replay | Tue 17 Dec | Tranmere Rvs. | 2 - 1 | York City |
| League Cup | 1st Round | Tue 27 Aug | York City | 1 - 2 | Bolton Wdrs. |
| Bolton Wanderers won 4-3 on aggregate |
| (Associate Members) | Northern Section Preliminary Round Group Seven | Tue 07 Jan | Stockport Co. | 3 - 0 | York City |
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| 1990/1991 | F.A. Cup | 2nd Round | Mon 17 Dec | Mansfield Town | 2 - 1 | York City |
| League Cup | 1st Round | Tue 04 Sep | Wrexham | 2 - 0 | York City |
| Wrexham won 3-0 on aggregate |
| (Associate Members) | Northern Section 1st Round | Tue 22 Jan | York City | 1 - 2 | Bury |
|
| 1989/1990 | F.A. Cup | 1st Round | Sat 18 Nov | York City | 1 - 2 | Grimsby Town |
| League Cup | 2nd Round | Tue 03 Oct | Southampton | 2 - 0 | York City |
| Southampton won 3-0 on aggregate |
| (Associate Members) | Northern Section 1st Round | Tue 09 Jan | Halifax Town | 1 - 1 | York City |
| after extra time, 90 minutes 0-0, Halifax Town won 7-6 on penalties |
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| 1988/1989 | F.A. Cup | 1st Round | Sat 19 Nov | Halifax Town | 1 - 0 | York City |
| League Cup | 1st Round | Tue 06 Sep | Sunderland | 4 - 0 | York City |
| Sunderland won 4-0 on aggregate |
| (Associate Members) | Northern Section 1st Round | Sat 07 Jan | Scarborough | 3 - 1 | York City |
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| 1987/1988 | F.A. Cup | 2nd Round Replay | Wed 09 Dec | Hartlepool U. | 3 - 1 | York City |
| League Cup | 2nd Round | Tue 06 Oct | York City | 0 - 4 | Leeds Utd. |
| Leeds United won 5-1 on aggregate |
| (Associate Members) | Northern Section Preliminary Round Group Five | Tue 24 Nov | Chesterfield | 2 - 0 | York City |
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| 1986/1987 | F.A. Cup | 2nd Round Replay | Tue 09 Dec | York City | 1 - 2 | Caernarfon T. |
| League Cup | 2nd Round | Wed 08 Oct | Chelsea | 3 - 0 | York City |
| Chelsea won 3-1 on aggregate |
| (Associate Members) | Northern Section 1st Round | Tue 27 Jan | York City | 0 - 1 | Mansfield Town |
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| 1985/1986 | F.A. Cup | 5th Round Replay | Tue 18 Feb | Liverpool | 3 - 1 | York City |
| after extra time, 90 minutes ?-? |
| League Cup | 2nd Round | Tue 08 Oct | York City | 2 - 3 | Grimsby Town |
| Grimsby Town won 4-3 on aggregate |
| (Associate Members) | Northern Section Preliminary Round Group Seven | Tue 28 Jan | Hartlepool U. | 3 - 2 | York City |
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| 1984/1985 | F.A. Cup | 5th Round Replay | Wed 20 Feb | Liverpool | 7 - 0 | York City |
| League Cup | 2nd Round | Tue 09 Oct | Q.P.R. | 4 - 1 | York City |
| Queens Park Rangers won 8-3 on aggregate |
| (Associate Members) | Northern Section Quarter-Final | Mon 22 Apr | York City | 2 - 3 | Lincoln City |
|
| 1983/1984 | F.A. Cup | 2nd Round | Sat 10 Dec | York City | 0 - 2 | Rochdale |
| League Cup | 1st Round | Tue 13 Sep | Grimsby Town | 2 - 0 | York City |
| Grimsby Town won 3-2 on aggregate |
| (Associate Members) | Northern Section 1st Round | Tue 21 Feb | York City | 1 - 2 | Hull City |
|
| 1982/1983 | F.A. Cup | 3rd Round | Sat 08 Jan | Crystal Palace | 2 - 1 | York City |
| League Cup | 1st Round | Wed 15 Sep | Lincoln City | 3 - 1 | York City |
| Lincoln City won 4-3 on aggregate |
|
| 1981/1982 | F.A. Cup | 2nd Round Replay | Sat 02 Jan | Altrincham | 4 - 3 | York City |
| League Cup | 1st Round | Tue 15 Sep | York City | 1 - 1 | Sheff. Utd. |
| Sheffield United won 2-1 on aggregate |
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| 1980/1981 | F.A. Cup | 1st Round Replay | Tue 25 Nov | York City | 1 - 2 | Tranmere Rvs. |
| after extra time, 90 minutes ?-? |
| League Cup | 2nd Round | Wed 03 Sep | Bristol Rvs. | 1 - 0 | York City |
| aggregate 2-2, Bristol Rovers won on away goals rule |
|
| 1979/1980 | F.A. Cup | 2nd Round Replay | Tue 18 Dec | York City | 0 - 2 | Bury |
| League Cup | 1st Round | Tue 14 Aug | York City | 3 - 2 | Mansfield Town |
| aggregate 3-3, Mansfield Town won on away goals rule |
|
| 1978/1979 | F.A. Cup | 4th Round | Sat 27 Jan | Nottm. Forest | 3 - 1 | York City |
| League Cup | 1st Round | Tue 15 Aug | York City | 0 - 3 | Grimsby Town |
| Grimsby Town won 5-0 on aggregate |
|
| 1977/1978 | F.A. Cup | 1st Round | Sat 26 Nov | Wigan Ath. | 1 - 0 | York City |
| League Cup | 1st Round Replay | Tue 23 Aug | York City | 1 - 1 | Rotherham U. |
| after extra time, 90 minutes 1-1, Rotherham United won 6-5 on penalties |
|
| 1976/1977 | F.A. Cup | 2nd Round 2nd Replay | Tue 21 Dec | Rotherham U. | 2 - 1 | York City |
| after extra time, 90 minutes ?-? |
| League Cup | 1st Round Replay | Tue 24 Aug | York City | 1 - 2 | Barnsley |
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| 1975/1976 | F.A. Cup | 4th Round | Sat 24 Jan | York City | 0 - 2 | Chelsea |
| League Cup | 2nd Round | Wed 10 Sep | York City | 0 - 1 | Liverpool |
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| 1974/1975 | F.A. Cup | 3rd Round Replay | Tue 07 Jan | York City | 1 - 3 | Arsenal |
| after extra time, 90 minutes ?-? |
| League Cup | 1st Round | Wed 21 Aug | York City | 0 - 2 | Huddersfield |
|
| 1973/1974 | F.A. Cup | 1st Round Replay | Mon 10 Dec | Mansfield Town | 5 - 3 | York City |
| League Cup | 4th Round Replay | Wed 05 Dec | Man. City | 4 - 1 | York City |
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| 1972/1973 | F.A. Cup | 3rd Round | Sat 13 Jan | York City | 0 - 1 | Oxford Utd. |
| League Cup | 1st Round | Wed 16 Aug | Notts. County | 3 - 1 | York City |
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| 1971/1972 | F.A. Cup | 2nd Round Replay | Mon 13 Dec | York City | 2 - 3 | Rotherham U. |
| after extra time, 90 minutes ?-? |
| League Cup | 3rd Round | Tue 05 Oct | Sheff. Utd. | 3 - 2 | York City |
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| 1970/1971 | F.A. Cup | 4th Round Replay | Mon 01 Feb | Southampton | 3 - 2 | York City |
| League Cup | 2nd Round 2nd Replay | Mon 28 Sep | York City | 1 - 2 | Northampton |
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| 1969/1970 | F.A. Cup | 4th Round | Sat 24 Jan | Middlesbrough | 4 - 1 | York City |
| League Cup | 1st Round | Wed 13 Aug | Darlington | 3 - 0 | York City |
|
| 1968/1969 | F.A. Cup | 3rd Round | Sat 04 Jan | York City | 0 - 2 | Stoke City |
| League Cup | 1st Round | Wed 14 Aug | York City | 3 - 4 | Barnsley |
|
| 1967/1968 | F.A. Cup | 1st Round | Sat 09 Dec | York City | 0 - 1 | Doncaster Rvs. |
| League Cup | 1st Round | Wed 23 Aug | Darlington | 1 - 0 | York City |
|
| 1966/1967 | F.A. Cup | 2nd Round 2nd Replay | Mon 16 Jan | Middlesbrough | 4 - 1 | York City |
| played at neutral ground |
| League Cup | 3rd Round | Tue 04 Oct | York City | 0 - 2 | Blackburn R. |
|
| 1965/1966 | F.A. Cup | 1st Round | Sat 13 Nov | South Shields | 3 - 1 | York City |
| League Cup | 2nd Round | Wed 22 Sep | Millwall | 4 - 1 | York City |
|
| 1964/1965 | F.A. Cup | 2nd Round | Sat 05 Dec | Chesterfield | 2 - 1 | York City |
| League Cup | 1st Round | Wed 02 Sep | Bradford City | 2 - 0 | York City |
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| 1963/1964 | F.A. Cup | 1st Round | Sat 16 Nov | York City | 2 - 5 | Carlisle Utd. |
| League Cup | 2nd Round Replay | Mon 14 Oct | Lincoln City | 2 - 0 | York City |
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| 1962/1963 | F.A. Cup | 3rd Round | Wed 13 Feb | Southampton | 5 - 0 | York City |
| League Cup | 1st Round Replay | Wed 19 Sep | Lincoln City | 2 - 0 | York City |
|
| 1961/1962 | F.A. Cup | 1st Round | Sat 04 Nov | Bradford City | 1 - 0 | York City |
| League Cup | Quarter Final | Wed 07 Feb | Rochdale | 2 - 1 | York City |
|
| 1960/1961 | F.A. Cup | 3rd Round Replay | Wed 11 Jan | Norwich City | 1 - 0 | York City |
| League Cup | 1st Round | Mon 10 Oct | York City | 1 - 3 | Blackburn R. |
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| 1959/1960 | F.A. Cup | 3rd Round | Sat 09 Jan | Bournemouth & Boscombe Ath. | 1 - 0 | York City |
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| 1958/1959 | F.A. Cup | 1st Round | Tue 18 Nov | Bury | 1 - 0 | York City |
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| 1957/1958 | F.A. Cup | 4th Round Replay | Wed 29 Jan | Bolton Wdrs. | 3 - 0 | York City |
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| 1956/1957 | F.A. Cup | 2nd Round | Sat 08 Dec | Hull City | 2 - 1 | York City |
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| 1955/1956 | F.A. Cup | 4th Round Replay | Wed 01 Feb | Sunderland | 2 - 1 | York City |
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| 1954/1955 | F.A. Cup | Semi Final Replay | Wed 30 Mar | Newcastle Utd. | 2 - 0 | York City |
| played at Roker Park |
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| 1953/1954 | F.A. Cup | 1st Round | Sat 21 Nov | Barnsley | 5 - 2 | York City |
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| 1952/1953 | F.A. Cup | 1st Round | Sat 22 Nov | York City | 1 - 2 | Barrow |
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| 1951/1952 | F.A. Cup | 1st Round 2nd Replay | Mon 03 Dec | York City | 0 - 4 | Bradford P.A. |
| played at neutral ground |
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| 1950/1951 | F.A. Cup | 3rd Round | Sat 06 Jan | Bolton Wdrs. | 2 - 0 | York City |
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| 1949/1950 | F.A. Cup | 1st Round | Sat 26 Nov | Gateshead | 3 - 1 | York City |
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| 1948/1949 | F.A. Cup | 2nd Round Replay | Sat 18 Dec | York City | 0 - 2 | Southport |
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| 1947/1948 | F.A. Cup | 1st Round | Sat 29 Nov | York City | 0 - 1 | Rochdale |
|
| 1946/1947 | F.A. Cup | 1st Round | Sat 30 Nov | York City | 0 - 1 | Scunthorpe U. |
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| 1945/1946 | F.A. Cup | 4th Round | Wed 30 Jan | York City | 1 - 6 | Sheff. Wed. |
| Sheffield Wednesday won 11-2 on aggregate |
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| 1938/1939 | F.A. Cup | 3rd Round | Wed 11 Jan | York City | 0 - 5 | Millwall |
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| 1937/1938 | F.A. Cup | 6th Round Replay | Wed 09 Mar | Huddersfield | 2 - 1 | York City |
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| 1936/1937 | F.A. Cup | 4th Round Replay | Wed 03 Feb | York City | 1 - 3 | Swansea Town |
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| 1935/1936 | F.A. Cup | 1st Round | Sat 30 Nov | York City | 1 - 5 | Burton Town |
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| 1934/1935 | F.A. Cup | 3rd Round | Sat 12 Jan | York City | 0 - 1 | Derby County |
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| 1933/1934 | F.A. Cup | 1st Round | Sat 25 Nov | York City | 2 - 3 | Hartlepools |
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| 1932/1933 | F.A. Cup | 1st Round | Sat 26 Nov | York City | 1 - 3 | Scarborough |
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| 1931/1932 | F.A. Cup | 1st Round | Sat 28 Nov | New Brighton | 3 - 1 | York City |
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| 1930/1931 | F.A. Cup | 3rd Round Replay | Wed 14 Jan | York City | 0 - 2 | Sheff. Utd. |
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| 1929/1930 | F.A. Cup | 3rd Round Replay | Wed 15 Jan | York City | 1 - 2 | Newcastle Utd. |
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| 1928/1929 | F.A. Cup | 1st Round | Sat 24 Nov | York City | 0 - 1 | Barrow |
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| 1926/1927 | F.A. Cup | 2nd Round | Sat 11 Dec | Grimsby Town | 2 - 1 | York City |
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