FA Cup 2021/22, First Round Proper |
 | 16.11.2021 |  | Cheltenham Town | – | Gillingham | | 1:0 (1:0) * |
| Cheltenham |
FA Cup 2020/21, Third Round Proper |
| 10.01.2021 | | Cheltenham Town | – | Mansfield Town | | 2:1 aet
(0:1, 1:1) * |
| Cheltenham |
FA Cup 2020/21, Second Round Proper |
| 28.11.2020 | | Cheltenham Town | – | Crewe Alexandra | | 2:1 aet
(1:0, 1:1) * |
| Cheltenham |
FA Cup 2020/21, First Round Proper |
| 07.11.2020 | | Cheltenham Town | – | South Shields | | 3:1 (1:1) * |
| Cheltenham |
FA Cup 2019/20, First Round Proper |
| 19.11.2019 | | Swindon Town | – | Cheltenham Town | | 0:1 (0:0) * |
| Swindon |
FA Cup 2018/19, First Round Proper |
| 20.11.2018 | | Cheltenham Town | – | Ebbsfleet United | | 2:0 (0:0) * |
| Cheltenham |
FA Cup 2016/17, First Round Proper |
| 15.11.2016 | | Crewe Alexandra | – | Cheltenham Town | | 1:4 (0:2) * |
| Crewe |
FA Cup 2015/16, Fourth Qualifying Round |
| 27.10.2015 | | Cheltenham Town | – | Havant & Waterlooville | | 1:0 (0:0) * |
| Cheltenham |
FA Cup 2014/15, First Round Proper |
| 08.11.2014 | | Cheltenham Town | – | Swindon Town | | 5:0 (2:0) |
| Cheltenham |
FA Cup 2012/13, Second Round Proper |
| 11.12.2012 | | Hereford United | – | Cheltenham Town | | 1:2 aet
(0:1, 1:1) * |
| Hereford |
FA Cup 2012/13, First Round Proper |
| 03.11.2012 | | Cheltenham Town | – | Yate Town | | 3:0 (1:0) |
| Cheltenham |
FA Cup 2011/12, Second Round Proper |
| 03.12.2011 | | Luton Town | – | Cheltenham Town | | 2:4 (1:2) |
| Luton |
FA Cup 2011/12, First Round Proper |
| 12.11.2011 | | Tranmere Rovers | – | Cheltenham Town | | 0:1 (0:1) |
| Birkenhead |
FA Cup 2010/11, First Round Proper |
| 06.11.2010 | | Cheltenham Town | – | Morecambe | | 1:0 (0:0) |
| Cheltenham |
FA Cup 2008/09, Second Round Proper |
| 02.12.2008 | | Morecambe | – | Cheltenham Town | | 2:3 (2:2) |
| |
FA Cup 2008/09, First Round Proper |
| 18.11.2008 | | Oldham Athletic | – | Cheltenham Town | | 0:1 (0:1) * |
| Oldham |
FA Cup 2005/06, Third Round Proper |
| 17.01.2006 | | Chester City | – | Cheltenham Town | | 0:1 (0:0) * |
| Chester |
FA Cup 2005/06, Second Round Proper |
| 13.12.2005 | | Oxford United | – | Cheltenham Town | | 1:2 (0:0) * |
| Oxford |
FA Cup 2005/06, First Round Proper |
| 05.11.2005 | | Cheltenham Town | – | Carlisle United | | 1:0 (0:0) |
| Cheltenham |
FA Cup 2003/04, Second Round Proper |
| 06.12.2003 | | Cheltenham Town | – | Leyton Orient | | 3:1 (2:0) |
| Cheltenham |
FA Cup 2003/04, First Round Proper |
| 08.11.2003 | | Cheltenham Town | – | Hull City | | 3:1 (1:0) |
| Cheltenham |
FA Cup 2002/03, Second Round Proper |
| 07.12.2002 | | Oldham Athletic | – | Cheltenham Town | | 1:2 (0:2) |
| Oldham |
FA Cup 2002/03, First Round Proper |
| 16.11.2002 | | Yeovil Town | – | Cheltenham Town | | 0:2 (0:1) |
| Yeovil |
FA Cup 2001/02, Fourth Round Proper |
| 27.01.2002 | | Cheltenham Town | – | Burnley | | 2:1 (2:1) |
| Cheltenham |
FA Cup 2001/02, Third Round Proper |
| 06.01.2002 | | Cheltenham Town | – | Oldham Athletic | | 2:1 (1:1) |
| Cheltenham |
FA Cup 2001/02, Second Round Proper |
| 08.12.2001 | | Hinckley United | – | Cheltenham Town | | 0:2 (0:1) |
| |
FA Cup 2001/02, First Round Proper |
| 17.11.2001 | | Kettering Town | – | Cheltenham Town | | 1:6 (1:2) |
| Kettering |
FA Cup 2000/01, First Round Proper |
| 18.11.2000 | | Cheltenham Town | – | Shrewsbury Town | | 4:1 (1:1) |
| Cheltenham |
FA Cup 1998/99, Fourth Qualifying Round |
| | | Cheltenham Town | – | Taunton Town | | 3:2 |
| |
FA Cup 1998/99, Third Qualifying Round |
| | | Barnstaple Town | – | Cheltenham Town | | 0:1 |
| |
FA Cup 1997/98, Second Round Proper |
| 16.12.1997 | | Boreham Wood | – | Cheltenham Town | | 0:2 (0:1) * |
| |
FA Cup 1997/98, First Round Proper |
| 15.11.1997 | | Cheltenham Town | – | Tiverton Town | | 2:1 (1:1) |
| |
FA Cup 1997/98, Fourth Qualifying Round |
| | | Cheltenham Town | – | Sutton United | | 1:0 |
| |
FA Cup 1997/98, Third Qualifying Round |
| | | Cheltenham Town | – | Paulton Rovers | | 5:0 |
| |
FA Cup 1997/98, Second Qualifying Round |
| |  | Merthyr Tydfil | – | Cheltenham Town | | 0:2 |
| |
FA Cup 1997/98, First Qualifying Round |
| | | Thatcham Town | – | Cheltenham Town | | 0:1 |
| |
FA Cup 1996/97, Fourth Qualifying Round |
| | | Cheltenham Town | – | Bath City | | 4:1 * |
| |
FA Cup 1996/97, Third Qualifying Round |
| | | Cheltenham Town | – | Weymouth | | 1:0 |
| |
FA Cup 1996/97, Second Qualifying Round |
| | | Cheltenham Town | – | Salisbury City | | 4:3 |
| |
FA Cup 1996/97, First Qualifying Round |
| | | Gosport Borough | – | Cheltenham Town | | 0:1 |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Cheltenham Town | – | Yate Town | | 5:0 |
| |
FA Cup 1992/93, First Round Proper |
| 14.11.1992 | | St Albans City | – | Cheltenham Town | | 1:2 (0:0) |
| |
FA Cup 1992/93, Fourth Qualifying Round |
| | | Cheltenham Town | – | Worthing | | 3:2 |
| |
FA Cup 1992/93, Third Qualifying Round |
| | | AFC Lymington | – | Cheltenham Town | | 0:1 |
| |
FA Cup 1992/93, Second Qualifying Round |
| | | Cheltenham Town | – | Cinderford Town | | 3:0 |
| |
FA Cup 1992/93, First Qualifying Round |
| | | Cheltenham Town | – | Waterlooville | | 2:0 * |
| |
FA Cup 1991/92, Second Qualifying Round |
| | | Cheltenham Town | – | Taunton Town | | 8:0 |
| |
FA Cup 1991/92, First Qualifying Round |
| | | Cheltenham Town | – | Bridgend Town | | 5:0 * |
| |
FA Cup 1990/91, Fourth Qualifying Round |
| | | Dorking | – | Cheltenham Town | | 2:3 |
| |
FA Cup 1990/91, Third Qualifying Round |
| | | Cheltenham Town | – | Worcester City | | 4:2 |
| |
FA Cup 1990/91, Second Qualifying Round |
| | | Weston-Super-Mare | – | Cheltenham Town | | 0:2 |
| |
FA Cup 1990/91, First Qualifying Round |
| | | Cheltenham Town | – | Exmouth Town | | 3:0 * |
| |
FA Cup 1989/90, Second Qualifying Round |
| | | Cheltenham Town | – | Weston-Super-Mare | | 7:0 |
| |
FA Cup 1989/90, First Qualifying Round |
| | | Cheltenham Town | – | Saltash United | | 1:0 |
| |
FA Cup 1988/89, First Qualifying Round |
| | | Radstock Town | – | Cheltenham Town | | 0:2 |
| |
FA Cup 1987/88, Fourth Qualifying Round |
| | | Cheltenham Town | – | Bracknell Town | | 2:1 |
| |
FA Cup 1987/88, Third Qualifying Round |
| | | Weston-Super-Mare | – | Cheltenham Town | | 1:2 |
| |
FA Cup 1987/88, Second Qualifying Round |
| | | Cheltenham Town | – | Mangotsfield United | | 2:0 * |
| |
FA Cup 1987/88, First Qualifying Round |
| | | Cheltenham Town | – | Dorchester Town | | 4:1 |
| |
FA Cup 1984/85, Second Qualifying Round |
| | | Ton Pentre | – | Cheltenham Town | | 2:3 |
| |
FA Cup 1984/85, First Qualifying Round |
| | | Bideford | – | Cheltenham Town | | 0:2 * |
| |
FA Cup 1983/84, Third Qualifying Round |
| | | Cheltenham Town | – | Barry Town | | 3:1 |
| |
FA Cup 1983/84, Second Qualifying Round |
| | | Bridgend Town | – | Cheltenham Town | | 0:2 |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Cheltenham Town | – | Glastonbury | | 4:0 * |
| |
FA Cup 1982/83, Third Qualifying Round |
| | | Cheltenham Town | – | Trowbridge Town | | 1:0 * |
| |
FA Cup 1982/83, Second Qualifying Round |
| | | Cheltenham Town | – | Gloucester City | | 5:1 |
| |
FA Cup 1982/83, First Qualifying Round |
| | | Thame United | – | Cheltenham Town | | 2:3 |
| |
FA Cup 1981/82, Third Qualifying Round |
| | | Cheltenham Town | – | Haverfordwest County | | 4:0 |
| |
FA Cup 1981/82, Second Qualifying Round |
| | | Bath City | – | Cheltenham Town | | 1:2 * |
| |
FA Cup 1981/82, First Qualifying Round |
| | | Cheltenham Town | – | Barry Town | | 4:0 |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Cheltenham Town | – | Forest Green Rovers | | 3:2 |
| |
FA Cup 1980/81, Preliminary Round |
| | | Oxford City | – | Cheltenham Town | | 0:2 |
| |
FA Cup 1979/80, First Qualifying Round |
| | | Paulton Rovers | – | Cheltenham Town | | 0:2 |
| |
FA Cup 1979/80, Preliminary Round |
| | | Devizes Town | – | Cheltenham Town | | 0:1 |
| |
FA Cup 1978/79, Third Qualifying Round |
| | | Trowbridge Town | – | Cheltenham Town | | 0:4 |
| |
FA Cup 1978/79, Second Qualifying Round |
| | | Cheltenham Town | – | Melksham Town | | 6:0 |
| |
FA Cup 1978/79, First Qualifying Round |
| | | Cheltenham Town | – | Clevedon Town | | 6:1 |
| |
FA Cup 1977/78, First Qualifying Round |
| | | Cheltenham Town | – | Atherstone Town | | 1:0 * |
| |
FA Cup 1977/78, Preliminary Round |
| | | Cheltenham Town | – | Moor Green | | 4:1 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Cheltenham Town | – | Ton Pentre | | 4:0 * |
| |
FA Cup 1975/76, Third Qualifying Round |
| | | Cheltenham Town | – | Oxford City | | 2:0 * |
| |
FA Cup 1975/76, Second Qualifying Round |
| | | Cheltenham Town | – | Banbury United | | 2:0 |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Desborough Town | – | Cheltenham Town | | 2:3 * |
| |
FA Cup 1974/75, Fourth Qualifying Round |
| | | Cheltenham Town | – | Salisbury | | 4:1 |
| |
FA Cup 1974/75, Third Qualifying Round |
| | | Cheltenham Town | – | Cinderford Town | | 3:2 |
| |
FA Cup 1974/75, Second Qualifying Round |
| | | Cheltenham Town | – | Gloucester City | | 4:1 |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Cheltenham Town | – | Llanelli | | 3:2 |
| |
FA Cup 1972/73, Second Qualifying Round |
| | | Cheltenham Town | – | Trowbridge Town | | 4:0 |
| |
FA Cup 1972/73, First Qualifying Round |
| | | Cheltenham Town | – | Bath City | | 3:2 * |
| |
FA Cup 1970/71, Fourth Qualifying Round |
| | | Burton Albion | – | Cheltenham Town | | 0:3 * |
| |
FA Cup 1969/70, Fourth Qualifying Round |
| | | Cheltenham Town | – | Glastonbury | | 4:1 * |
| |
FA Cup 1968/69, Fourth Qualifying Round |
| | | Frome Town | – | Cheltenham Town | | 1:2 |
| |
FA Cup 1968/69, Third Qualifying Round |
| | | Cinderford Town | – | Cheltenham Town | | 1:3 |
| |
FA Cup 1968/69, Second Qualifying Round |
| | | Cheltenham Town | – | Abergavenny Thursdays | | 3:2 * |
| |
FA Cup 1968/69, First Qualifying Round |
| | | Cheltenham Town | – | Lovells Athletic | | 2:1 |
| |
FA Cup 1967/68, Third Qualifying Round |
| | | Cheltenham Town | – | Barry Town | | 3:1 * |
| |
FA Cup 1967/68, Second Qualifying Round |
| | | Gloucester City | – | Cheltenham Town | | 0:1 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Cheltenham Town | – | Merthyr Tydfil | | 2:1 |
| |
FA Cup 1966/67, Third Qualifying Round |
| | | Cinderford Town | – | Cheltenham Town | | 2:3 |
| |
FA Cup 1966/67, Second Qualifying Round |
| | | Merthyr Tydfil | – | Cheltenham Town | | 1:3 |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Lovells Athletic | – | Cheltenham Town | | 0:3 |
| |
FA Cup 1965/66, Third Qualifying Round |
| | | Devizes Town | – | Cheltenham Town | | 2:8 |
| |
FA Cup 1965/66, Second Qualifying Round |
| | | Cheltenham Town | – | Chippenham Town | | 4:1 |
| |
FA Cup 1964/65, Third Qualifying Round |
| | | Cheltenham Town | – | Devizes Town | | 6:1 |
| |
FA Cup 1964/65, Second Qualifying Round |
| | | Trowbridge Town | – | Cheltenham Town | | 1:3 |
| |
FA Cup 1964/65, First Qualifying Round |
| | | Melksham Town | – | Cheltenham Town | | 0:4 |
| |
FA Cup 1963/64, Second Qualifying Round |
| | | Gloucester City | – | Cheltenham Town | | 1:2 |
| |
FA Cup 1963/64, First Qualifying Round |
| | | Cheltenham Town | – | Abergavenny Thursdays | | 7:2 |
| |
FA Cup 1962/63, Fourth Qualifying Round |
| | | Minehead | – | Cheltenham Town | | 0:1 |
| |
FA Cup 1962/63, Third Qualifying Round |
| | | Gloucester City | – | Cheltenham Town | | 1:2 |
| |
FA Cup 1962/63, Second Qualifying Round |
| | | Cheltenham Town | – | Lovells Athletic | | 5:1 |
| |
FA Cup 1962/63, First Qualifying Round |
| | | Cheltenham Town | – | Llanelli | | 1:0 |
| |
FA Cup 1961/62, Third Qualifying Round |
| | | Cheltenham Town | – | Chippenham Town | | 2:0 |
| |
FA Cup 1961/62, Second Qualifying Round |
| | | Cheltenham Town | – | Melksham Town | | 5:2 |
| |
FA Cup 1961/62, First Qualifying Round |
| | | Chippenham United | – | Cheltenham Town | | 2:6 |
| |
FA Cup 1960/61, Third Qualifying Round |
| | | Cheltenham Town | – | Llanelli | | 2:0 |
| |
FA Cup 1960/61, Second Qualifying Round |
| | | Cheltenham Town | – | Merthyr Tydfil | | 4:0 |
| |
FA Cup 1960/61, First Qualifying Round |
| | | Gloucester City | – | Cheltenham Town | | 1:4 |
| |
FA Cup 1959/60, Fourth Qualifying Round |
| | | Bridgwater Town | – | Cheltenham Town | | 0:1 * |
| |
FA Cup 1959/60, Third Qualifying Round |
| | | Barry Town | – | Cheltenham Town | | 1:4 |
| |
FA Cup 1959/60, Second Qualifying Round |
| | | Merthyr Tydfil | – | Cheltenham Town | | 0:1 * |
| |
FA Cup 1959/60, First Qualifying Round |
| | | Gloucester City | – | Cheltenham Town | | 1:3 |
| |
FA Cup 1959/60, Preliminary Round |
| | | Cheltenham Town | – | Lovells Athletic | | 1:0 |
| |
FA Cup 1956/57, Fourth Qualifying Round |
| | | Cheltenham Town | – | Andover | | 2:1 |
| |
FA Cup 1956/57, Third Qualifying Round |
| | | Cheltenham Town | – | Llanelli | | 4:0 |
| |
FA Cup 1956/57, Second Qualifying Round |
| | | Gloucester City | – | Cheltenham Town | | 1:2 |
| |
FA Cup 1956/57, First Qualifying Round |
| | | Ebbw Vale | – | Cheltenham Town | | 2:5 |
| |
FA Cup 1956/57, Preliminary Round |
| | | Cheltenham Town | – | Lovells Athletic | | 3:0 |
| |
FA Cup 1952/53, First Qualifying Round |
| | | Cheltenham Town | – | Cinderford Town | | 5:0 * |
| |
FA Cup 1950/51, Fourth Qualifying Round |
| | | Yeovil Town | – | Cheltenham Town | | 2:4 |
| |
FA Cup 1947/48, First Round Proper |
| 29.11.1947 | | Cheltenham Town | – | Street | | 5:0 |
| |
FA Cup 1947/48, Fourth Qualifying Round |
| | | Kidderminster Harriers | – | Cheltenham Town | | 2:4 |
| |
FA Cup 1946/47, Fourth Qualifying Round |
| | | Hereford United | – | Cheltenham Town | | 3:4 * |
| |
FA Cup 1945/46, Fourth Qualifying Round |
| | | Peasedown Miners Welfare | – | Cheltenham Town | | 0:1 * |
| |
FA Cup 1933/34, Second Round Proper |
| 09.12.1933 | | Carlisle United | – | Cheltenham Town | | 1:2 |
| |
FA Cup 1933/34, First Round Proper |
| 25.11.1933 | | Cheltenham Town | – | Barnet | | 5:1 |
| |
