FA Cup 2021/22, First Round Proper |
 | 06.11.2021 | | Gillingham | – | Cheltenham Town | | 1:1 (0:1) |
| Gillingham |
FA Cup 2019/20, First Round Proper |
| 09.11.2019 | | Cheltenham Town | – | Swindon Town | | 1:1 (0:0) |
| Cheltenham |
FA Cup 2018/19, First Round Proper |
| 10.11.2018 | | Ebbsfleet United | – | Cheltenham Town | | 0:0 |
| Northfleet |
FA Cup 2016/17, First Round Proper |
| 05.11.2016 | | Cheltenham Town | – | Crewe Alexandra | | 1:1 (0:0) |
| Cheltenham |
FA Cup 2015/16, Fourth Qualifying Round |
| 24.10.2015 | | Havant & Waterlooville | – | Cheltenham Town | | 3:3 (0:1) |
| Havant |
FA Cup 2012/13, Second Round Proper |
| 03.12.2012 | | Cheltenham Town | – | Hereford United | | 1:1 (1:1) |
| Cheltenham |
FA Cup 2008/09, Third Round Proper |
| 13.01.2009 | | Cheltenham Town | – | Doncaster Rovers | | 0:0 |
| Cheltenham |
FA Cup 2008/09, First Round Proper |
| 08.11.2008 | | Cheltenham Town | – | Oldham Athletic | | 2:2 (2:0) |
| Cheltenham |
FA Cup 2007/08, First Round Proper |
| 10.11.2007 | | Cheltenham Town | – | Brighton & Hove Albion | | 1:1 (0:0) |
| Cheltenham |
FA Cup 2006/07, First Round Proper |
| 10.11.2006 | | Cheltenham Town | – | Scunthorpe United | | 0:0 |
| Cheltenham |
FA Cup 2005/06, Third Round Proper |
| 07.01.2006 | | Cheltenham Town | – | Chester City | | 2:2 (0:0) |
| Cheltenham |
FA Cup 2005/06, Second Round Proper |
| 03.12.2005 | | Cheltenham Town | – | Oxford United | | 1:1 (1:0) |
| Cheltenham |
FA Cup 1999/00, First Round Proper |
| 30.10.1999 | | Cheltenham Town | – | Gillingham | | 1:1 (0:1) |
| Cheltenham |
FA Cup 1997/98, Third Round Proper |
| 13.01.1998 | | Cheltenham Town | – | Reading | | 1:1 (1:0) |
| Cheltenham |
FA Cup 1997/98, Second Round Proper |
| 06.12.1997 | | Cheltenham Town | – | Boreham Wood | | 1:1 (0:1) |
| |
FA Cup 1996/97, First Round Proper |
| 16.11.1996 | | Peterborough United | – | Cheltenham Town | | 0:0 |
| Peterborough |
FA Cup 1996/97, Fourth Qualifying Round |
| | | Bath City | – | Cheltenham Town | | 0:0 |
| |
FA Cup 1994/95, Fourth Qualifying Round |
| | | Cheltenham Town | – | Bashley | | 1:1 |
| |
FA Cup 1993/94, Fourth Qualifying Round |
| | | Cheltenham Town | – | Bath City | | 1:1 |
| |
FA Cup 1992/93, Second Round Proper |
| 05.12.1992 | | Cheltenham Town | – | Bournemouth | | 1:1 (0:1) |
| |
FA Cup 1992/93, First Qualifying Round |
| | | Waterlooville | – | Cheltenham Town | | 0:0 |
| |
FA Cup 1991/92, First Qualifying Round |
| | | Bridgend Town | – | Cheltenham Town | | 3:3 |
| |
FA Cup 1990/91, First Qualifying Round |
| | | Exmouth Town | – | Cheltenham Town | | 3:3 aet * |
| |
FA Cup 1990/91, First Qualifying Round |
| | | Cheltenham Town | – | Exmouth Town | | 2:2 |
| |
FA Cup 1987/88, Second Qualifying Round |
| | | Mangotsfield United | – | Cheltenham Town | | 1:1 |
| |
FA Cup 1985/86, First Qualifying Round |
| | | Minehead | – | Cheltenham Town | | 1:1 |
| |
FA Cup 1984/85, First Qualifying Round |
| | | Cheltenham Town | – | Bideford | | 0:0 |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Glastonbury | – | Cheltenham Town | | 0:0 |
| |
FA Cup 1982/83, Fourth Qualifying Round |
| | | Cheltenham Town | – | Weymouth | | 0:0 |
| |
FA Cup 1982/83, Third Qualifying Round |
| | | Trowbridge Town | – | Cheltenham Town | | 1:1 |
| |
FA Cup 1981/82, Second Qualifying Round |
| | | Cheltenham Town | – | Bath City | | 2:2 |
| |
FA Cup 1977/78, First Qualifying Round |
| | | Atherstone Town | – | Cheltenham Town | | 0:0 |
| |
FA Cup 1976/77, Second Qualifying Round |
| | | Cheltenham Town | – | Merthyr Tydfil | | 1:1 aet * |
| |
FA Cup 1976/77, Second Qualifying Round |
| | | Merthyr Tydfil | – | Cheltenham Town | | 3:3 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Ton Pentre | – | Cheltenham Town | | 1:1 |
| |
FA Cup 1975/76, Third Qualifying Round |
| | | Oxford City | – | Cheltenham Town | | 0:0 |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Cheltenham Town | – | Desborough Town | | 1:1 |
| |
FA Cup 1972/73, First Qualifying Round |
| | | Bath City | – | Cheltenham Town | | 0:0 |
| |
FA Cup 1970/71, Fourth Qualifying Round |
| | | Cheltenham Town | – | Burton Albion | | 2:2 |
| |
FA Cup 1969/70, Fourth Qualifying Round |
| | | Glastonbury | – | Cheltenham Town | | 0:0 |
| |
FA Cup 1968/69, Second Qualifying Round |
| | | Abergavenny Thursdays | – | Cheltenham Town | | 2:2 |
| |
FA Cup 1967/68, Third Qualifying Round |
| | | Barry Town | – | Cheltenham Town | | 2:2 |
| |
FA Cup 1966/67, Fourth Qualifying Round |
| | | Cheltenham Town | – | Yeovil Town | | 3:3 |
| |
FA Cup 1960/61, Fourth Qualifying Round |
| | | Bridgwater Town | – | Cheltenham Town | | 0:0 |
| |
FA Cup 1959/60, First Round Proper |
| 14.11.1959 | | Cheltenham Town | – | Watford | | 0:0 |
| |
FA Cup 1959/60, Fourth Qualifying Round |
| | | Cheltenham Town | – | Bridgwater Town | | 0:0 |
| |
FA Cup 1959/60, Second Qualifying Round |
| | | Cheltenham Town | – | Merthyr Tydfil | | 2:2 |
| |
FA Cup 1957/58, First Qualifying Round |
| | | Lovells Athletic | – | Cheltenham Town | | 0:0 aet * |
| |
FA Cup 1957/58, First Qualifying Round |
| | | Cheltenham Town | – | Lovells Athletic | | 0:0 |
| |
FA Cup 1954/55, First Qualifying Round |
| | | Barry Town | – | Cheltenham Town | | 1:1 |
| |
FA Cup 1952/53, First Qualifying Round |
| | | Cinderford Town | – | Cheltenham Town | | 1:1 |
| |
FA Cup 1949/50, Fourth Qualifying Round |
| | | Cheltenham Town | – | Hereford United | | 2:2 aet * |
| |
FA Cup 1949/50, Fourth Qualifying Round |
| | | Hereford United | – | Cheltenham Town | | 1:1 |
| |
FA Cup 1946/47, Fourth Qualifying Round |
| | | Cheltenham Town | – | Hereford United | | 1:1 |
| |
FA Cup 1945/46, Fourth Qualifying Round |
| | | Cheltenham Town | – | Peasedown Miners Welfare | | 1:1 |
| |
FA Cup 1938/39, First Round Proper |
| 26.11.1938 | | Cheltenham Town | – | Cardiff City | | 1:1 |
| |
FA Cup 1935/36, First Round Proper |
| 30.11.1935 | | Brighton & Hove Albion | – | Cheltenham Town | | 0:0 |
| |
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