| Season |
Competition |
Round Reached |
Date |
Home |
|
Away |
| 2011/2012 | F.A. Cup | 3rd Round | Sat 07 Jan | Tottenham H. | 3 - 0 | Cheltenham T. |
| League Cup | 1st Round | Tue 09 Aug | Cheltenham T. | 1 - 4 | Milton Keynes |
| (Associate Members) | Southern Section Quarter-Final | Tue 08 Nov | Cheltenham T. | 0 - 2 | Barnet |
| 2010/2011 | F.A. Cup | 2nd Round | Sat 27 Nov | Southampton | 3 - 0 | Cheltenham T. |
| League Cup | 1st Round | Tue 10 Aug | Brentford | 2 - 1 | Cheltenham T. |
| (Associate Members) | Southern Section 2nd Round | Tue 05 Oct | Cheltenham T. | 0 - 2 | Plymouth Arg. |
| 2009/2010 | F.A. Cup | 1st Round | Sat 07 Nov | Torquay Utd. | 3 - 1 | Cheltenham T. |
| League Cup | 1st Round | Tue 11 Aug | Cheltenham T. | 1 - 2 | Southend Utd. |
| (Associate Members) | Southern Section 1st Round | Tue 01 Sep | Cheltenham T. | 1 - 3 | Torquay Utd. |
| 2008/2009 | F.A. Cup | 3rd Round Replay | Tue 20 Jan | Doncaster Rvs. | 3 - 0 | Cheltenham T. |
| League Cup | 2nd Round | Tue 26 Aug | Cheltenham T. | 2 - 3 | Stoke City |
| (Associate Members) | Southern Section 2nd Round | Tue 07 Oct | Cheltenham T. | 1 - 2 | Walsall |
| 2007/2008 | F.A. Cup | 1st Round Replay | Tue 20 Nov | Brighton & HA | 2 - 1 | Cheltenham T. |
| League Cup | 1st Round | Tue 14 Aug | Southend Utd. | 4 - 1 | Cheltenham T. |
| after extra time, 90 minutes 1-1 |
| (Associate Members) | Southern Section Quarter-Final | Wed 14 Nov | Brighton & HA | 4 - 1 | Cheltenham T. |
| 2006/2007 | F.A. Cup | 1st Round Replay | Tue 21 Nov | Scunthorpe U. | 2 - 0 | Cheltenham T. |
| League Cup | 2nd Round | Tue 19 Sep | West Brom. | 3 - 1 | Cheltenham T. |
| (Associate Members) | Southern Section Quarter-Final | Tue 28 Nov | Cheltenham T. | 2 - 3 | Shrewsbury Tn. |
| 2005/2006 | F.A. Cup | 4th Round | Sat 28 Jan | Cheltenham T. | 0 - 2 | Newcastle Utd. |
| League Cup | 2nd Round | Tue 20 Sep | Sunderland | 1 - 0 | Cheltenham T. |
| after extra time, 90 minutes 0-0 |
| (Associate Members) | Southern Section Semi-Final | Tue 24 Jan | Cheltenham T. | 0 - 1 | Colchester U. |
| 2004/2005 | F.A. Cup | 1st Round | Sun 14 Nov | Cheltenham T. | 1 - 3 | Swansea City |
| League Cup | 1st Round | Tue 24 Aug | Colchester U. | 2 - 1 | Cheltenham T. |
| (Associate Members) | Southern Section 2nd Round | Tue 02 Nov | Cheltenham T. | 2 - 2 | Walsall |
| after extra time, 90 minutes 1-1, Walsall won 4-3 on penalties |
| 2003/2004 | F.A. Cup | 3rd Round | Sun 04 Jan | Fulham | 2 - 1 | Cheltenham T. |
| League Cup | 1st Round | Tue 12 Aug | Cheltenham T. | 1 - 2 | Q.P.R. |
| (Associate Members) | Southern Section 1st Round | Tue 14 Oct | Cheltenham T. | 1 - 3 | Colchester U. |
| 2002/2003 | F.A. Cup | 3rd Round | Sat 04 Jan | Sheff. Utd. | 4 - 0 | Cheltenham T. |
| League Cup | 2nd Round | Wed 02 Oct | Crystal Palace | 7 - 0 | Cheltenham T. |
| (Associate Members) | Southern Section 2nd Round | Tue 12 Nov | Cheltenham T. | 1 - 2 | Wycombe Wdrs. |
| after extra time, 90 minutes 1-1, Wycombe Wanderers won on golden goal rule |
| 2001/2002 | F.A. Cup | 5th Round | Sat 16 Feb | West Brom. | 1 - 0 | Cheltenham T. |
| League Cup | 1st Round | Tue 21 Aug | Bristol City | 2 - 1 | Cheltenham T. |
| (Associate Members) | Southern Section 2nd Round | Tue 30 Oct | Cambridge U. | 1 - 1 | Cheltenham T. |
| after extra time, 90 minutes 1-1, Cambridge United won 5-4 on penalties |
| 2000/2001 | F.A. Cup | 2nd Round | Sat 09 Dec | Cardiff City | 3 - 1 | Cheltenham T. |
| League Cup | 1st Round | Tue 05 Sep | Cheltenham T. | 0 - 3 | Watford |
| (Associate Members) | Southern Section 1st Round | Tue 05 Dec | Southend Utd. | 2 - 0 | Cheltenham T. |
| 1999/2000 | F.A. Cup | 1st Round Replay | Tue 09 Nov | Gillingham | 3 - 2 | Cheltenham T. |
| League Cup | 1st Round | Tue 24 Aug | Cheltenham T. | 2 - 1 | Norwich City |
| after extra time, 90 minutes 2-0, Norwich City won 3-2 on aggregate |
| (Associate Members) | Southern Section 2nd Round | Wed 12 Jan | Bristol City | 3 - 1 | Cheltenham T. |
| 1998/1999 | F.A. Cup | 1st Round | Sat 14 Nov | Cheltenham T. | 0 - 1 | Lincoln City |
| 1997/1998 | F.A. Cup | 3rd Round Replay | Tue 20 Jan | Reading | 2 - 1 | Cheltenham T. |
| 1996/1997 | F.A. Cup | 1st Round Replay | Wed 27 Nov | Cheltenham T. | 1 - 3 | Peterborough |
| after extra time, 90 minutes 0-0 |
| 1992/1993 | F.A. Cup | 2nd Round Replay | Wed 16 Dec | Bournemouth | 3 - 0 | Cheltenham T. |
| 1990/1991 | F.A. Cup | 1st Round | Sat 17 Nov | Birmingham C. | 1 - 0 | Cheltenham T. |
| 1987/1988 | F.A. Cup | 1st Round | Sat 14 Nov | Wolves | 5 - 1 | Cheltenham T. |
| 1974/1975 | F.A. Cup | 1st Round | Sat 23 Nov | Wycombe Wdrs. | 3 - 1 | Cheltenham T. |
| 1970/1971 | F.A. Cup | 1st Round | Sat 21 Nov | Brighton & HA | 4 - 0 | Cheltenham T. |
| 1969/1970 | F.A. Cup | 1st Round | Sat 15 Nov | Cheltenham T. | 0 - 2 | Oxford City |
| 1968/1969 | F.A. Cup | 1st Round | Sat 16 Nov | Cheltenham T. | 0 - 4 | Watford |
| 1962/1963 | F.A. Cup | 1st Round | Sat 03 Nov | Cheltenham T. | 3 - 6 | Enfield |
| 1959/1960 | F.A. Cup | 1st Round Replay | Tue 17 Nov | Watford | 3 - 0 | Cheltenham T. |
| 1956/1957 | F.A. Cup | 1st Round | Sat 17 Nov | Cheltenham T. | 1 - 2 | Reading |
| 1950/1951 | F.A. Cup | 1st Round | Sat 25 Nov | Reading | 3 - 1 | Cheltenham T. |
| 1947/1948 | F.A. Cup | 2nd Round | Sat 13 Dec | Hull City | 4 - 2 | Cheltenham T. |
| 1946/1947 | F.A. Cup | 1st Round | Sat 30 Nov | Aldershot Tn. | 4 - 2 | Cheltenham T. |
| 1945/1946 | F.A. Cup | 1st Round | Sat 24 Nov | Cheltenham T. | 0 - 2 | Bath City |
| Bath City won 5-2 on aggregate |
| 1938/1939 | F.A. Cup | 1st Round Replay | Wed 30 Nov | Cardiff City | 1 - 0 | Cheltenham T. |
| 1937/1938 | F.A. Cup | 1st Round | Sat 27 Nov | Watford | 3 - 0 | Cheltenham T. |
| 1935/1936 | F.A. Cup | 1st Round Replay | Wed 04 Dec | Cheltenham T. | 0 - 6 | Brighton & HA |
| 1933/1934 | F.A. Cup | 3rd Round | Sat 13 Jan | Cheltenham T. | 1 - 3 | Blackpool |
