FA Cup 2023/24, First Round Proper |
 | 04.11.2023 |  | AFC Wimbledon | – | Cheltenham Town | | 5:1 (2:0) |
| London |
FA Cup 2022/23, First Round Proper |
| 05.11.2022 | | Cheltenham Town | – | Alvechurch | | 1:2 (0:1) |
| Cheltenham |
FA Cup 2021/22, Second Round Proper |
| 04.12.2021 | | AFC Wimbledon | – | Cheltenham Town | | 4:3 (2:1) |
| London |
FA Cup 2020/21, Fourth Round Proper |
| 23.01.2021 | | Cheltenham Town | – | Manchester City | | 1:3 (0:0) * |
| Cheltenham |
FA Cup 2019/20, Second Round Proper |
| 30.11.2019 | | Cheltenham Town | – | Port Vale | | 1:3 (1:0) |
| Cheltenham |
FA Cup 2018/19, Second Round Proper |
| 01.12.2018 | | Accrington Stanley | – | Cheltenham Town | | 3:1 (0:0) |
| Accrington |
FA Cup 2017/18, First Round Proper |
| 04.11.2017 | | Cheltenham Town | – | Maidstone United | | 2:4 (0:3) |
| Cheltenham |
FA Cup 2016/17, Second Round Proper |
| 03.12.2016 | | Sutton United | – | Cheltenham Town | | 2:1 (0:1) |
| Sutton |
FA Cup 2015/16, First Round Proper |
| 07.11.2015 | | Hartlepool United | – | Cheltenham Town | | 1:0 (1:0) |
| Hartlepool |
FA Cup 2014/15, Second Round Proper |
| 07.12.2014 | | Cheltenham Town | – | Dover Athletic | | 0:1 (0:0) |
| Cheltenham |
FA Cup 2013/14, First Round Proper |
| 09.11.2013 | | Tamworth | – | Cheltenham Town | | 1:0 (1:0) |
| Tamworth |
FA Cup 2012/13, Third Round Proper |
| 07.01.2013 | | Cheltenham Town | – | Everton | | 1:5 (0:2) |
| Cheltenham |
FA Cup 2011/12, Third Round Proper |
| 07.01.2012 | | Tottenham Hotspur | – | Cheltenham Town | | 3:0 (2:0) |
| London |
FA Cup 2010/11, Second Round Proper |
| 27.11.2010 | | Southampton | – | Cheltenham Town | | 3:0 (1:0) |
| Southampton |
FA Cup 2009/10, First Round Proper |
| 07.11.2009 | | Torquay United | – | Cheltenham Town | | 3:1 (2:1) |
| Torquay |
FA Cup 2008/09, Third Round Proper |
| 20.01.2009 | | Doncaster Rovers | – | Cheltenham Town | | 3:0 (2:0) * |
| Doncaster |
FA Cup 2007/08, First Round Proper |
| 20.11.2007 | | Brighton & Hove Albion | – | Cheltenham Town | | 2:1 (1:0) * |
| Brighton & Hove |
FA Cup 2006/07, First Round Proper |
| 21.11.2006 | | Scunthorpe United | – | Cheltenham Town | | 2:0 (1:0) * |
| Scunthorpe |
FA Cup 2005/06, Fourth Round Proper |
| 28.01.2006 | | Cheltenham Town | – | Newcastle United | | 0:2 (0:2) |
| Cheltenham |
FA Cup 2004/05, First Round Proper |
| 14.11.2004 | | Cheltenham Town | – | Swansea City |  | 1:3 (0:1) |
| Cheltenham |
FA Cup 2003/04, Third Round Proper |
| 04.01.2004 | | Fulham | – | Cheltenham Town | | 2:1 (1:1) |
| London |
FA Cup 2002/03, Third Round Proper |
| 04.01.2003 | | Sheffield United | – | Cheltenham Town | | 4:0 (2:0) |
| Sheffield |
FA Cup 2001/02, Fifth Round Proper |
| 16.02.2002 | | West Bromwich Albion | – | Cheltenham Town | | 1:0 (0:0) |
| West Bromwich |
FA Cup 2000/01, Second Round Proper |
| 09.12.2000 | | Cardiff City | – | Cheltenham Town | | 3:1 (2:1) |
| Cardiff |
FA Cup 1999/00, First Round Proper |
| 09.11.1999 | | Gillingham | – | Cheltenham Town | | 3:2 (2:0) * |
| Gillingham |
FA Cup 1998/99, First Round Proper |
| 14.11.1998 | | Cheltenham Town | – | Lincoln City | | 0:1 (0:0) |
| Cheltenham |
FA Cup 1997/98, Third Round Proper |
| 20.01.1998 | | Reading | – | Cheltenham Town | | 2:1 (1:0) * |
| Reading |
FA Cup 1996/97, First Round Proper |
| 27.11.1996 | | Cheltenham Town | – | Peterborough United | | 1:3 (0:0) * |
| Cheltenham |
FA Cup 1995/96, Second Qualifying Round |
| | | Forest Green Rovers | – | Cheltenham Town | | 3:0 |
| |
FA Cup 1994/95, Fourth Qualifying Round |
| | | Bashley | – | Cheltenham Town | | 2:1 * |
| |
FA Cup 1993/94, Fourth Qualifying Round |
| | | Bath City | – | Cheltenham Town | | 4:2 * |
| |
FA Cup 1992/93, Second Round Proper |
| 16.12.1992 | | Bournemouth | – | Cheltenham Town | | 3:0 (1:0) * |
| |
FA Cup 1991/92, Third Qualifying Round |
| | | Weymouth | – | Cheltenham Town | | 4:0 |
| |
FA Cup 1990/91, First Round Proper |
| 17.11.1990 | | Birmingham City | – | Cheltenham Town | | 1:0 |
| Birmingham |
FA Cup 1989/90, Third Qualifying Round |
| | | Dorchester Town | – | Cheltenham Town | | 2:1 |
| |
FA Cup 1988/89, Second Qualifying Round |
| | | Gloucester City | – | Cheltenham Town | | 3:0 |
| |
FA Cup 1987/88, First Round Proper |
| 14.11.1987 | | Wolverhampton Wanderers | – | Cheltenham Town | | 5:1 (2:1) |
| Wolverhampton |
FA Cup 1986/87, First Qualifying Round |
| | | Cheltenham Town | – | Bideford | | 3:4 |
| |
FA Cup 1985/86, First Qualifying Round |
| | | Cheltenham Town | – | Minehead | | 1:2 * |
| |
FA Cup 1984/85, Third Qualifying Round |
| | | Merthyr Tydfil | – | Cheltenham Town | | 4:1 |
| |
FA Cup 1983/84, Fourth Qualifying Round |
| | | Windsor & Eton | – | Cheltenham Town | | 1:0 |
| |
FA Cup 1982/83, Fourth Qualifying Round |
| | | Weymouth | – | Cheltenham Town | | 4:0 * |
| |
FA Cup 1981/82, Fourth Qualifying Round |
| | | Cheltenham Town | – | Dorchester Town | | 1:3 |
| |
FA Cup 1980/81, Second Qualifying Round |
| | | Buckingham Town | – | Cheltenham Town | | 2:1 |
| |
FA Cup 1979/80, Second Qualifying Round |
| | | Cheltenham Town | – | Merthyr Tydfil | | 0:2 |
| |
FA Cup 1978/79, Fourth Qualifying Round |
| | | Cheltenham Town | – | Yeovil Town | | 1:2 |
| |
FA Cup 1977/78, Second Qualifying Round |
| | | Burton Albion | – | Cheltenham Town | | 2:1 |
| |
FA Cup 1976/77, Second Qualifying Round |
| | | Merthyr Tydfil | – | Cheltenham Town | | 4:0 * |
| |
FA Cup 1975/76, Fourth Qualifying Round |
| | | Nuneaton Borough | – | Cheltenham Town | | 2:1 |
| |
FA Cup 1974/75, First Round Proper |
| 23.11.1974 | | Wycombe Wanderers | – | Cheltenham Town | | 3:1 |
| |
FA Cup 1972/73, Third Qualifying Round |
| | | Devizes Town | – | Cheltenham Town | | 1:0 |
| |
FA Cup 1971/72, Fourth Qualifying Round |
| | | Hereford United | – | Cheltenham Town | | 3:0 |
| |
FA Cup 1970/71, First Round Proper |
| 21.11.1970 | | Brighton & Hove Albion | – | Cheltenham Town | | 4:0 |
| |
FA Cup 1969/70, First Round Proper |
| 15.11.1969 | | Cheltenham Town | – | Oxford City | | 0:2 (0:1) |
| |
FA Cup 1968/69, First Round Proper |
| 16.11.1968 | | Cheltenham Town | – | Watford | | 0:4 |
| |
FA Cup 1967/68, Fourth Qualifying Round |
| | | Hereford United | – | Cheltenham Town | | 3:2 |
| |
FA Cup 1966/67, Fourth Qualifying Round |
| | | Yeovil Town | – | Cheltenham Town | | 3:1 * |
| |
FA Cup 1965/66, Fourth Qualifying Round |
| | | Cheltenham Town | – | Hereford United | | 0:1 |
| |
FA Cup 1964/65, Fourth Qualifying Round |
| | | Bideford | – | Cheltenham Town | | 1:0 |
| |
FA Cup 1963/64, Third Qualifying Round |
| | | Cheltenham Town | – | Llanelli | | 0:1 |
| |
FA Cup 1962/63, First Round Proper |
| 03.11.1962 | | Cheltenham Town | – | Enfield | | 3:6 |
| |
FA Cup 1961/62, Fourth Qualifying Round |
| | | Cheltenham Town | – | Weston-Super-Mare | | 0:1 |
| |
FA Cup 1960/61, Fourth Qualifying Round |
| | | Cheltenham Town | – | Bridgwater Town | | 1:2 * |
| |
FA Cup 1959/60, First Round Proper |
| 17.11.1959 | | Watford | – | Cheltenham Town | | 3:0 * |
| |
FA Cup 1958/59, Preliminary Round |
| | | Barry Town | – | Cheltenham Town | | 2:0 |
| |
FA Cup 1957/58, First Qualifying Round |
| | | Cheltenham Town | – | Lovells Athletic | | 2:4 * |
| |
FA Cup 1956/57, First Round Proper |
| 17.11.1956 | | Cheltenham Town | – | Reading | | 1:2 |
| |
FA Cup 1955/56, First Qualifying Round |
| | | Cheltenham Town | – | Lovells Athletic | | 1:2 |
| |
FA Cup 1954/55, First Qualifying Round |
| | | Cheltenham Town | – | Barry Town | | 1:2 * |
| |
FA Cup 1953/54, First Qualifying Round |
| | | Merthyr Tydfil | – | Cheltenham Town | | 3:2 |
| |
FA Cup 1952/53, Second Qualifying Round |
| | | Cheltenham Town | – | Barry Town | | 0:3 |
| |
FA Cup 1951/52, Fourth Qualifying Round |
| | | Cheltenham Town | – | Merthyr Tydfil | | 2:3 |
| |
FA Cup 1950/51, First Round Proper |
| 25.11.1950 | | Reading | – | Cheltenham Town | | 3:1 |
| |
FA Cup 1949/50, Fourth Qualifying Round |
| | | Hereford United | – | Cheltenham Town | | 4:2 * |
| |
FA Cup 1948/49, Fourth Qualifying Round |
| | | Wellington Town | – | Cheltenham Town | | 2:1 |
| |
FA Cup 1947/48, Second Round Proper |
| 13.12.1947 | | Hull City | – | Cheltenham Town | | 4:2 |
| |
FA Cup 1946/47, First Round Proper |
| 30.11.1946 | | Aldershot | – | Cheltenham Town | | 4:2 |
| |
FA Cup 1945/46, First Round Proper |
| 24.11.1945 | | Cheltenham Town | – | Bath City | | 0:2 |
| |
FA Cup 1945/46, First Round Proper |
| 17.11.1945 | | Bath City | – | Cheltenham Town | | 3:2 |
| |
FA Cup 1938/39, First Round Proper |
| 30.11.1938 | | Cardiff City | – | Cheltenham Town | | 1:0 * |
| |
FA Cup 1937/38, First Round Proper |
| 27.11.1937 | | Watford | – | Cheltenham Town | | 3:0 |
| |
FA Cup 1935/36, First Round Proper |
| 04.12.1935 | | Cheltenham Town | – | Brighton & Hove Albion | | 0:6 * |
| |
FA Cup 1933/34, Third Round Proper |
| 13.01.1934 | | Cheltenham Town | – | Blackpool | | 1:3 |
| |
