| Season | Competition |
Round Reached | Date |
Home | |
Away |
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| 2007/2008 | F.A. Cup | 3rd Round Replay | Tue 15 Jan | Liverpool | 5 - 0 | Luton Town |
| League Cup | 4th Round | Wed 31 Oct | Luton Town | 0 - 1 | Everton |
| after extra time |
| (Associate Members) | Southern Section 2nd Round | Tue 09 Oct | Gillingham | 4 - 3 | Luton Town |
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| 2006/2007 | F.A. Cup | 4th Round | Sat 27 Jan | Luton Town | 0 - 4 | Blackburn R. |
| League Cup | 3rd Round | Tue 24 Oct | Everton | 4 - 0 | Luton Town |
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| 2005/2006 | F.A. Cup | 3rd Round | Sat 07 Jan | Luton Town | 3 - 5 | Liverpool |
| League Cup | 2nd Round | Tue 20 Sep | Reading | 1 - 0 | Luton Town |
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| 2004/2005 | F.A. Cup | 3rd Round | Sat 08 Jan | Luton Town | 0 - 2 | Brentford |
| League Cup | 1st Round | Tue 07 Sep | Boston Utd. | 4 - 3 | Luton Town |
| after extra time, 90 minutes 3-3 |
| (Associate Members) | Southern Section 1st Round | Tue 28 Sep | Swansea City | 2 - 0 | Luton Town |
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| 2003/2004 | F.A. Cup | 4th Round | Sat 24 Jan | Luton Town | 0 - 1 | Tranmere Rvs. |
| League Cup | 2nd Round | Tue 23 Sep | Charlton Ath. | 4 - 4 | Luton Town |
| after extra time, 90 minutes 3-3, Charlton Athletic won 8-7 on penalties |
| (Associate Members) | Southern Section Quarter-Final | Tue 09 Dec | Southend Utd. | 3 - 0 | Luton Town |
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| 2002/2003 | F.A. Cup | 2nd Round | Sat 07 Dec | Wigan Ath. | 3 - 0 | Luton Town |
| League Cup | 2nd Round | Wed 02 Oct | Aston Villa | 3 - 0 | Luton Town |
| (Associate Members) | Southern Section Quarter-Final | Tue 10 Dec | Luton Town | 1 - 2 | Cambridge U. |
| after extra time, 90 minutes 1-1, Cambridge United won on the golden goal rule |
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| 2001/2002 | F.A. Cup | 1st Round | Sat 17 Nov | Southend Utd. | 3 - 2 | Luton Town |
| League Cup | 1st Round | Tue 21 Aug | Reading | 4 - 0 | Luton Town |
| (Associate Members) | Southern Section 2nd Round | Tue 30 Oct | Dag. & Red. | 3 - 2 | Luton Town |
| after extra time, 90 minutes 2-2, Dagenham & Redbridge won on golden goal rule |
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| 2000/2001 | F.A. Cup | 3rd Round Replay | Wed 17 Jan | Q.P.R. | 2 - 1 | Luton Town |
| after extra time, 90 minutes 1-1 |
| League Cup | 2nd Round | Tue 26 Sep | Luton Town | 1 - 2 | Sunderland |
| (Associate Members) | Southern Section 1st Round | Tue 05 Dec | Peterborough | 1 - 0 | Luton Town |
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| 1999/2000 | F.A. Cup | 3rd Round Replay | Tue 21 Dec | Luton Town | 0 - 3 | Fulham |
| League Cup | 1st Round | Wed 25 Aug | Bristol Rvs. | 2 - 2 | Luton Town |
| Bristol Rovers won 4-2 on aggregate |
| (Associate Members) | Southern Section 1st Round | Tue 07 Dec | Oxford Utd. | 2 - 0 | Luton Town |
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| 1998/1999 | F.A. Cup | 2nd Round | Sat 05 Dec | Luton Town | 1 - 2 | Hull City |
| League Cup | Quarter Final | Tue 01 Dec | Sunderland | 3 - 0 | Luton Town |
| (Associate Members) | Southern Section 2nd Round | Tue 05 Jan | Luton Town | 0 - 3 | Walsall |
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| 1997/1998 | F.A. Cup | 1st Round | Sat 15 Nov | Luton Town | 0 - 1 | Torquay Utd. |
| League Cup | 2nd Round | Tue 23 Sep | West Brom. | 4 - 2 | Luton Town |
| West Bromwich Albion won 5-3 on aggregate |
| (Associate Members) | Southern Section Semi-Final | Tue 17 Feb | Bournemouth | 1 - 0 | Luton Town |
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| 1996/1997 | F.A. Cup | 3rd Round Replay | Sat 25 Jan | Bolton Wdrs. | 6 - 2 | Luton Town |
| League Cup | 3rd Round Replay | Tue 12 Nov | Luton Town | 1 - 2 | Wimbledon |
| after extra time, 90 minutes 1-1 |
| (Associate Members) | Southern Section 2nd Round | Tue 04 Feb | Northampton | 1 - 0 | Luton Town |
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| 1995/1996 | F.A. Cup | 3rd Round | Sat 06 Jan | Grimsby Town | 7 - 1 | Luton Town |
| League Cup | 1st Round | Tue 22 Aug | Bournemouth | 2 - 1 | Luton Town |
| after extra time, 90 minutes 1-1, Bournemouth won 3-2 on aggregate |
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| 1994/1995 | F.A. Cup | 4th Round Replay | Wed 08 Feb | Southampton | 6 - 0 | Luton Town |
| League Cup | 1st Round | Tue 23 Aug | Fulham | 1 - 1 | Luton Town |
| after extra time, 90 minutes 1-1, aggregate 2-2, Fulham won 4-3 on penalties |
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| 1993/1994 | F.A. Cup | Semi Final | Sat 09 Apr | Chelsea | 2 - 0 | Luton Town |
| played at Wembley |
| League Cup | 1st Round | Tue 24 Aug | Luton Town | 0 - 1 | Cambridge U. |
| Cambridge United won 2-0 on aggregate |
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| 1992/1993 | F.A. Cup | 4th Round | Sat 23 Jan | Luton Town | 1 - 5 | Derby County |
| League Cup | 2nd Round | Tue 06 Oct | Plymouth Arg. | 3 - 2 | Luton Town |
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| 1991/1992 | F.A. Cup | 3rd Round | Sat 04 Jan | Sheff. Utd. | 4 - 0 | Luton Town |
| League Cup | 2nd Round | Tue 08 Oct | Birmingham C. | 3 - 2 | Luton Town |
| Birmingham City won 5-4 on aggregate |
| (Full Members) | Southern Section 2nd Round | Tue 22 Oct | Ipswich Town | 1 - 1 | Luton Town |
| after extra time, 90 minutes 1-1, Ipswich Town won 2-1 on penalties |
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| 1990/1991 | F.A. Cup | 4th Round Replay | Wed 30 Jan | West Ham Utd. | 5 - 0 | Luton Town |
| League Cup | 2nd Round | Wed 10 Oct | Bradford City | 1 - 1 | Luton Town |
| after extra time, 90 minutes 1-1, aggregate 2-2, Bradford City won 5-4 on penalties |
| (Full Members) | Southern Section Semi-Final | Tue 26 Feb | Crystal Palace | 3 - 1 | Luton Town |
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| 1989/1990 | F.A. Cup | 3rd Round | Sat 06 Jan | Brighton & HA | 4 - 1 | Luton Town |
| League Cup | 3rd Round | Tue 24 Oct | Everton | 3 - 0 | Luton Town |
| (Full Members) | Southern Section 2nd Round | Mon 27 Nov | Crystal Palace | 4 - 1 | Luton Town |
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| 1988/1989 | F.A. Cup | 3rd Round | Sat 07 Jan | Millwall | 3 - 2 | Luton Town |
| League Cup | Final | Sun 09 Apr | Nottm. Forest | 3 - 1 | Luton Town |
| played at Wembley |
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| 1987/1988 | F.A. Cup | Semi Final | Sat 09 Apr | Wimbledon | 2 - 1 | Luton Town |
| played at White Hart Lane |
| League Cup | Final | Sun 24 Apr | Luton Town | 3 - 2 | Arsenal |
| played at Wembley |
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| 1986/1987 | F.A. Cup | 4th Round Replay | Wed 04 Feb | Q.P.R. | 2 - 1 | Luton Town |
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| 1985/1986 | F.A. Cup | 6th Round Replay | Wed 12 Mar | Everton | 1 - 0 | Luton Town |
| League Cup | 3rd Round | Tue 29 Oct | Luton Town | 0 - 2 | Norwich City |
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| 1984/1985 | F.A. Cup | Semi Final | Sat 13 Apr | Everton | 2 - 1 | Luton Town |
| after extra time, 90 minutes ?-?; played at Villa Park |
| League Cup | 4th Round | Tue 20 Nov | Sheff. Wed. | 4 - 2 | Luton Town |
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| 1983/1984 | F.A. Cup | 3rd Round Replay | Tue 10 Jan | Watford | 4 - 3 | Luton Town |
| after extra time, 90 minutes ?-? |
| League Cup | 2nd Round | Tue 25 Oct | Luton Town | 0 - 2 | Rotherham U. |
| Rotherham United won 4-3 on aggregate |
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| 1982/1983 | F.A. Cup | 4th Round | Sat 29 Jan | Luton Town | 0 - 2 | Man. Utd. |
| League Cup | 4th Round | Wed 01 Dec | Tottenham H. | 1 - 0 | Luton Town |
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| 1981/1982 | F.A. Cup | 4th Round | Sat 23 Jan | Luton Town | 0 - 3 | Ipswich Town |
| League Cup | 2nd Round | Tue 27 Oct | Wrexham | 0 - 1 | Luton Town |
| Wrexham won 2-1 on aggregate |
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| 1980/1981 | F.A. Cup | 4th Round | Sat 24 Jan | Newcastle Utd. | 2 - 1 | Luton Town |
| League Cup | 3rd Round | Tue 23 Sep | Luton Town | 1 - 2 | Man. City |
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| 1979/1980 | F.A. Cup | 3rd Round | Sat 05 Jan | Luton Town | 0 - 2 | Swindon Town |
| League Cup | 1st Round | Tue 14 Aug | Luton Town | 1 - 1 | Gillingham |
| Gillingham won 4-1 on aggregate |
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| 1978/1979 | F.A. Cup | 3rd Round | Tue 09 Jan | York City | 2 - 0 | Luton Town |
| League Cup | Quarter Final | Wed 13 Dec | Leeds Utd. | 4 - 1 | Luton Town |
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| 1977/1978 | F.A. Cup | 4th Round | Tue 31 Jan | Millwall | 4 - 0 | Luton Town |
| League Cup | 3rd Round 2nd Replay | Wed 09 Nov | Luton Town | 2 - 3 | Man. City |
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| 1976/1977 | F.A. Cup | 4th Round | Sat 29 Jan | Chester | 1 - 0 | Luton Town |
| League Cup | 2nd Round | Tue 31 Aug | Sunderland | 3 - 1 | Luton Town |
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| 1975/1976 | F.A. Cup | 4th Round | Sat 24 Jan | Norwich City | 2 - 0 | Luton Town |
| League Cup | 2nd Round | Tue 09 Sep | Darlington | 2 - 1 | Luton Town |
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| 1974/1975 | F.A. Cup | 3rd Round | Sat 04 Jan | Luton Town | 0 - 1 | Birmingham C. |
| League Cup | 3rd Round | Tue 08 Oct | Sheff. Utd. | 2 - 0 | Luton Town |
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| 1973/1974 | F.A. Cup | 5th Round | Sat 16 Feb | Luton Town | 0 - 4 | Leicester City |
| League Cup | 4th Round | Wed 21 Nov | Millwall | 3 - 1 | Luton Town |
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| 1972/1973 | F.A. Cup | 6th Round | Sat 17 Mar | Sunderland | 2 - 0 | Luton Town |
| League Cup | 2nd Round 2nd Replay | Tue 19 Sep | Birmingham C. | 1 - 0 | Luton Town |
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| 1971/1972 | F.A. Cup | 3rd Round | Sat 15 Jan | West Ham Utd. | 2 - 1 | Luton Town |
| League Cup | 2nd Round | Tue 07 Sep | Crystal Palace | 2 - 0 | Luton Town |
| (Invitation) Cup | 1st Round | Sat 31 Jul | Colchester U. | 1 - 0 | Luton Town |
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| 1970/1971 | F.A. Cup | 3rd Round Replay | Mon 11 Jan | Luton Town | 3 - 4 | Nottm. Forest |
| League Cup | 3rd Round | Tue 06 Oct | Luton Town | 0 - 1 | Arsenal |
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| 1969/1970 | F.A. Cup | 2nd Round | Sat 06 Dec | Hillingdon B. | 2 - 1 | Luton Town |
| League Cup | 3rd Round | Tue 23 Sep | Sheff. Utd. | 3 - 0 | Luton Town |
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| 1968/1969 | F.A. Cup | 3rd Round | Sat 04 Jan | Man. City | 1 - 0 | Luton Town |
| League Cup | 3rd Round | Tue 24 Sep | Everton | 5 - 1 | Luton Town |
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| 1967/1968 | F.A. Cup | 2nd Round | Sat 06 Jan | Swindon Town | 3 - 2 | Luton Town |
| League Cup | 2nd Round | Wed 13 Sep | Leeds Utd. | 3 - 1 | Luton Town |
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| 1966/1967 | F.A. Cup | 2nd Round | Sat 07 Jan | Bristol Rvs. | 3 - 2 | Luton Town |
| League Cup | 1st Round Replay | Mon 29 Aug | Luton Town | 1 - 2 | Aldershot |
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| 1965/1966 | F.A. Cup | 2nd Round Replay | Tue 07 Dec | Luton Town | 0 - 1 | Corby Town |
| League Cup | 1st Round Replay | Tue 07 Sep | Brighton & HA | 2 - 0 | Luton Town |
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| 1964/1965 | F.A. Cup | 3rd Round | Sat 09 Jan | Luton Town | 0 - 3 | Sunderland |
| League Cup | 2nd Round | Wed 23 Sep | Luton Town | 0 - 1 | Aston Villa |
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| 1963/1964 | F.A. Cup | 3rd Round | Sat 04 Jan | Fulham | 4 - 1 | Luton Town |
| League Cup | 2nd Round | Wed 25 Sep | Luton Town | 3 - 4 | Coventry City |
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| 1962/1963 | F.A. Cup | 3rd Round | Sat 26 Jan | Luton Town | 0 - 2 | Swindon Town |
| League Cup | 4th Round | Wed 14 Nov | Man. City | 1 - 0 | Luton Town |
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| 1961/1962 | F.A. Cup | 3rd Round 2nd Replay | Mon 15 Jan | Ipswich Town | 5 - 1 | Luton Town |
| played at neutral ground |
| League Cup | 2nd Round Replay | Tue 10 Oct | Rotherham U. | 2 - 0 | Luton Town |
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| 1960/1961 | F.A. Cup | 5th Round | Sat 18 Feb | Barnsley | 1 - 0 | Luton Town |
| League Cup | 2nd Round Replay | Mon 24 Oct | Luton Town | 2 - 5 | Liverpool |
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| 1959/1960 | F.A. Cup | 5th Round | Sat 20 Feb | Luton Town | 1 - 4 | Wolves |
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| 1958/1959 | F.A. Cup | Final | Sat 02 May | Nottm. Forest | 2 - 1 | Luton Town |
| played at Wembley |
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| 1957/1958 | F.A. Cup | 3rd Round | Sat 04 Jan | Stockport Co. | 3 - 0 | Luton Town |
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| 1956/1957 | F.A. Cup | 3rd Round Replay | Mon 07 Jan | Aston Villa | 2 - 0 | Luton Town |
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| 1955/1956 | F.A. Cup | 3rd Round | Wed 11 Jan | Luton Town | 0 - 4 | Leicester City |
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| 1954/1955 | F.A. Cup | 5th Round | Sat 19 Feb | Luton Town | 0 - 2 | Man. City |
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| 1953/1954 | F.A. Cup | 3rd Round 3rd Replay | Mon 25 Jan | Luton Town | 0 - 2 | Blackpool |
| played at neutral ground |
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| 1952/1953 | F.A. Cup | 5th Round | Sat 14 Feb | Luton Town | 0 - 1 | Bolton Wdrs. |
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| 1951/1952 | F.A. Cup | 6th Round | Sat 08 Mar | Luton Town | 2 - 3 | Arsenal |
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| 1950/1951 | F.A. Cup | 4th Round | Sat 27 Jan | Luton Town | 1 - 2 | Bristol Rvs. |
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| 1949/1950 | F.A. Cup | 3rd Round | Sat 07 Jan | Luton Town | 3 - 4 | Grimsby Town |
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| 1948/1949 | F.A. Cup | 5th Round Replay | Sat 19 Feb | Leicester City | 5 - 3 | Luton Town |
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| 1947/1948 | F.A. Cup | 5th Round | Sat 07 Feb | Q.P.R. | 3 - 1 | Luton Town |
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| 1946/1947 | F.A. Cup | 5th Round Replay | Tue 11 Feb | Burnley | 3 - 0 | Luton Town |
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| 1945/1946 | F.A. Cup | 3rd Round | Wed 09 Jan | Derby County | 3 - 0 | Luton Town |
| Derby County won 9-0 on aggregate |
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| 1938/1939 | F.A. Cup | 3rd Round | Sat 07 Jan | Liverpool | 3 - 0 | Luton Town |
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| 1937/1938 | F.A. Cup | 5th Round | Sat 12 Feb | Luton Town | 1 - 3 | Man. City |
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| 1936/1937 | F.A. Cup | 4th Round Replay | Wed 03 Feb | Sunderland | 3 - 1 | Luton Town |
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| 1935/1936 | F.A. Cup | 4th Round | Sat 25 Jan | Man. City | 2 - 1 | Luton Town |
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| 1934/1935 | F.A. Cup | 4th Round | Sat 26 Jan | Burnley | 3 - 1 | Luton Town |
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| 1933/1934 | F.A. Cup | 3rd Round | Sat 13 Jan | Luton Town | 0 - 1 | Arsenal |
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| 1932/1933 | F.A. Cup | 6th Round | Sat 04 Mar | Everton | 6 - 0 | Luton Town |
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| 1931/1932 | F.A. Cup | 3rd Round | Sat 09 Jan | Luton Town | 1 - 2 | Wolves |
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| 1930/1931 | F.A. Cup | 2nd Round | Sat 13 Dec | Watford | 3 - 1 | Luton Town |
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| 1929/1930 | F.A. Cup | 1st Round | Sat 30 Nov | Luton Town | 2 - 3 | Q.P.R. |
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| 1928/1929 | F.A. Cup | 3rd Round Replay | Wed 16 Jan | Crystal Palace | 7 - 0 | Luton Town |
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| 1927/1928 | F.A. Cup | 3rd Round | Sat 14 Jan | Bolton Wdrs. | 2 - 1 | Luton Town |
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| 1926/1927 | F.A. Cup | 3rd Round | Sat 08 Jan | Chelsea | 4 - 0 | Luton Town |
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| 1925/1926 | F.A. Cup | 2nd Round | Sat 12 Dec | Aberdare | 1 - 0 | Luton Town |
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| 1924/1925 | F.A. Cup | 1st Round | Sat 10 Jan | West Brom. | 4 - 0 | Luton Town |
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| 1923/1924 | F.A. Cup | 1st Round | Sat 12 Jan | Arsenal | 4 - 1 | Luton Town |
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| 1922/1923 | F.A. Cup | 1st Round | Sat 13 Jan | Bury | 2 - 1 | Luton Town |
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| 1921/1922 | F.A. Cup | 2nd Round | Sat 28 Jan | Aston Villa | 1 - 0 | Luton Town |
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| 1920/1921 | F.A. Cup | 3rd Round | Sat 19 Feb | Luton Town | 2 - 3 | Preston N.E. |
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| 1919/1920 | F.A. Cup | 2nd Round | Sat 31 Jan | Luton Town | 0 - 2 | Liverpool |
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| 1914/1915 | F.A. Cup | 1st Round | Sat 09 Jan | Southampton | 3 - 0 | Luton Town |
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| 1911/1912 | F.A. Cup | 1st Round | Sat 13 Jan | Luton Town | 2 - 4 | Notts. County |
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| 1910/1911 | F.A. Cup | 1st Round | Sat 14 Jan | Northampton | 5 - 1 | Luton Town |
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| 1908/1909 | F.A. Cup | 1st Round | Sat 16 Jan | Luton Town | 1 - 2 | Millwall |
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| 1907/1908 | F.A. Cup | 1st Round | Sat 11 Jan | Luton Town | 3 - 8 | Fulham |
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| 1906/1907 | F.A. Cup | 2nd Round Replay | Wed 06 Feb | Sunderland | 1 - 0 | Luton Town |
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| 1902/1903 | F.A. Cup | 1st Round | Sat 07 Feb | Millwall | 3 - 0 | Luton Town |
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| 1897/1898 | F.A. Cup | 1st Round | Sat 29 Jan | Luton Town | 0 - 1 | Bolton Wdrs. |
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| 1896/1897 | F.A. Cup | 1st Round | Sat 30 Jan | Luton Town | 0 - 1 | West Brom. |
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| 1894/1895 | F.A. Cup | 1st Round | Sat 02 Feb | Luton Town | 0 - 2 | Preston N.E. |
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| 1893/1894 | F.A. Cup | 1st Round | Sat 27 Jan | Middlesbro Ir | 2 - 1 | Luton Town |
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| 1891/1892 | F.A. Cup | 1st Round | Sat 16 Jan | Luton Town | 0 - 3 | Middlesbrough |
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| 1887/1888 | F.A. Cup | 1st Round | Sat 15 Oct | Chatham | 5 - 1 | Luton Town |
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