FA Cup 2022/23, Second Qualifying Round |
 | 17.09.2022 |  | Hungerford Town | – | Gloucester City | | 1:3 (1:1) |
| Hungerford |
FA Cup 2021/22, Second qualifying round |
| 19.09.2021 | | Longlevens | – | Gloucester City | | 1:3 (1:1) |
| Cheltenham |
FA Cup 2019/20, Second Qualifying Round |
| 21.09.2019 | | Kidlington | – | Gloucester City | | 0:5 (0:1) |
| Kidlington |
FA Cup 2018/19, Third Qualifying Round |
| 09.10.2018 | | Dorking Wanderers | – | Gloucester City | | 0:3 (0:2) * |
| Dorking |
FA Cup 2018/19, Second Qualifying Round |
| 23.09.2018 | | Gloucester City | – | Plymouth Parkway | | 3:1 (1:1) |
| Cheltenham |
FA Cup 2016/17, Second Qualifying Round |
| 17.09.2016 | | Salisbury | – | Gloucester City | | 1:2 |
| |
FA Cup 2015/16, Third Qualifying Round |
| 10.10.2015 | | Leiston | – | Gloucester City | | 1:3 (0:1) |
| Leiston |
FA Cup 2015/16, Second Qualifying Round |
| 27.09.2015 | | Gloucester City | – | Kidlington | | 4:2 (3:0) |
| Cheltenham |
FA Cup 2014/15, Third Qualifying Round |
| 14.10.2014 | | Gloucester City | – | Staines Town | | 3:2 (1:0) * |
| Cheltenham |
FA Cup 2014/15, Second Qualifying Round |
| 30.09.2014 | | Gloucester City | – | Paulton Rovers | | 2:1 (1:0) * |
| Cheltenham |
FA Cup 2013/14, Fourth Qualifying Round |
| 26.10.2013 | | Gloucester City | – | Hampton & Richmond Borough | | 3:1 (0:1) |
| Cheltenham |
FA Cup 2013/14, Third Qualifying Round |
| 16.10.2013 | | Gloucester City | – | Yate Town | | 7:0 (4:0) * |
| Cheltenham |
FA Cup 2013/14, Second Qualifying Round |
| 01.10.2013 | | Havant & Waterlooville | – | Gloucester City | | 2:3 (1:1) * |
| Havant |
FA Cup 2012/13, Fourth Qualifying Round |
| 20.10.2012 | | Gloucester City | – | Chippenham Town | | 1:0 (0:0) |
| Cheltenham |
FA Cup 2012/13, Third Qualifying Round |
| 07.10.2012 | | Gloucester City | – | Eastleigh | | 1:0 (1:0) |
| Cheltenham |
FA Cup 2012/13, Second Qualifying Round |
| 22.09.2012 | | Gloucester City | – | Thatcham Town | | 2:1 (2:1) |
| Cheltenham |
FA Cup 2011/12, Third qualifying round |
| 15.10.2011 | | Gloucester City | – | Truro City | | 7:2 |
| Cheltenham |
FA Cup 2011/12, Second Qualifying Round |
| 01.10.2011 | | Whitchurch United | – | Gloucester City | | 0:2 |
| |
FA Cup 2009/10, Third Qualifying Round |
| 10.10.2009 | | Dorchester Town | – | Gloucester City | | 1:2 |
| |
FA Cup 2009/10, Second Qualifying Round |
| 26.09.2009 | | Bashley | – | Gloucester City | | 1:2 |
| |
FA Cup 2007/08, First Qualifying Round |
| 15.09.2007 | | Yate Town | – | Gloucester City | | 1:5 |
| |
FA Cup 2006/07, First Qualifying Round |
| 19.09.2006 | | Liskeard Athletic | – | Gloucester City | | 0:3 * |
| |
FA Cup 2003/04, Third Qualifying Round |
| | | Gloucester City | – | Chippenham Town | | 4:3 (1:2) |
| |
FA Cup 2003/04, Second Qualifying Round |
| | | Gloucester City | – | Merthyr Tydfil |  | 2:0 |
| |
FA Cup 2003/04, First Qualifying Round |
| | | Team Bath | – | Gloucester City | | 0:2 * |
| |
FA Cup 2003/04, Preliminary Round |
| | | Bristol Manor Farm | – | Gloucester City | | 0:5 |
| |
FA Cup 2002/03, First Qualifying Round |
| | | Gloucester City | – | Bashley | | 3:0 |
| |
FA Cup 2002/03, Preliminary Round |
| | | Minehead | – | Gloucester City | | 0:2 |
| |
FA Cup 2000/01, Third Qualifying Round |
| | | Tiverton Town | – | Gloucester City | | 1:3 |
| |
FA Cup 2000/01, Second Qualifying Round |
| | | Chippenham Town | – | Gloucester City | | 3:5 * |
| |
FA Cup 2000/01, First Qualifying Round |
| | | Gloucester City | – | Evesham United | | 2:1 |
| |
FA Cup 2000/01, Preliminary Round |
| | | Odd Down | – | Gloucester City | | 0:2 |
| |
FA Cup 1999/00, Second Qualifying Round |
| | | Gloucester City | – | Weymouth | | 2:1 * |
| |
FA Cup 1998/99, Third Qualifying Round |
| | | Gloucester City | – | Sudbury Town | | 10:0 |
| |
FA Cup 1998/99, Second Qualifying Round |
| | | Gloucester City | – | Paulton Rovers | | 2:1 |
| |
FA Cup 1997/98, Third Qualifying Round |
| | | Gloucester City | – | Waterlooville | | 2:0 |
| |
FA Cup 1997/98, Second Qualifying Round |
| | | Gloucester City | – | Newport IOW | | 2:1 |
| |
FA Cup 1997/98, First Qualifying Round |
| | | Gloucester City | – | Mangotsfield United | | 3:0 |
| |
FA Cup 1996/97, First Qualifying Round |
| | | Basingstoke Town | – | Gloucester City | | 0:3 |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Gloucester City | – | Bristol Manor Farm | | 8:0 |
| |
FA Cup 1994/95, Third Qualifying Round |
| | | Gloucester City | – | Cinderford Town | | 2:0 |
| |
FA Cup 1994/95, Second Qualifying Round |
| | | Gloucester City | – | Merthyr Tydfil | | 7:1 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | Gloucester City | – | Exmouth Town | | 3:0 |
| |
FA Cup 1991/92, First Qualifying Round |
| | | Gloucester City | – | Shortwood United | | 4:1 |
| |
FA Cup 1989/90, First Round Proper |
| 18.11.1989 | | Gloucester City | – | Dorchester Town | | 1:0 |
| |
FA Cup 1989/90, Fourth Qualifying Round |
| | | Folkestone | – | Gloucester City | | 0:1 |
| |
FA Cup 1989/90, Third Qualifying Round |
| | | Gloucester City | – | Worcester City | | 4:2 |
| |
FA Cup 1989/90, Second Qualifying Round |
| | | Gloucester City | – | Barry Town | | 2:0 * |
| |
FA Cup 1989/90, First Qualifying Round |
| | | Gloucester City | – | Mangotsfield United | | 4:0 |
| |
FA Cup 1988/89, Second Qualifying Round |
| | | Gloucester City | – | Cheltenham Town | | 3:0 |
| |
FA Cup 1988/89, First Qualifying Round |
| | | Melksham Town | – | Gloucester City | | 0:5 |
| |
FA Cup 1987/88, Preliminary Round |
| | | Gloucester City | – | Westbury United | | 7:0 |
| |
FA Cup 1984/85, First Qualifying Round |
| | | Llanelli | – | Gloucester City | | 2:5 |
| |
FA Cup 1983/84, Second Qualifying Round |
| | | Welton Rovers | – | Gloucester City | | 1:4 |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Haverfordwest County | – | Gloucester City | | 1:2 |
| |
FA Cup 1982/83, First Qualifying Round |
| | | Gloucester City | – | Llanelli | | 1:0 |
| |
FA Cup 1981/82, First Qualifying Round |
| | | Gloucester City | – | Forest Green Rovers | | 2:1 |
| |
FA Cup 1981/82, Preliminary Round |
| | | Clandown | – | Gloucester City | | 1:3 |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Gloucester City | – | Dorchester Town | | 1:0 |
| |
FA Cup 1978/79, Preliminary Round |
| | | Frome Town | – | Gloucester City | | 0:3 |
| |
FA Cup 1976/77, Preliminary Round |
| | | Trowbridge Town | – | Gloucester City | | 1:2 * |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Gloucester City | – | Merthyr Tydfil | | 3:2 |
| |
FA Cup 1968/69, Second Qualifying Round |
| | | Welton Rovers | – | Gloucester City | | 1:2 |
| |
FA Cup 1968/69, First Qualifying Round |
| | | Gloucester City | – | Devizes Town | | 3:1 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Lovells Athletic | – | Gloucester City | | 0:4 |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Gloucester City | – | Abergavenny Thursdays | | 4:1 |
| |
FA Cup 1965/66, Second Qualifying Round |
| | | Lovells Athletic | – | Gloucester City | | 1:2 |
| |
FA Cup 1965/66, First Qualifying Round |
| | | Gloucester City | – | Llanelli | | 1:0 |
| |
FA Cup 1964/65, First Qualifying Round |
| | | Gloucester City | – | Abergavenny Thursdays | | 3:1 |
| |
FA Cup 1963/64, First Qualifying Round |
| | | Merthyr Tydfil | – | Gloucester City | | 2:3 * |
| |
FA Cup 1962/63, Second Qualifying Round |
| | | Gloucester City | – | Barry Town | | 3:0 |
| |
FA Cup 1962/63, First Qualifying Round |
| | | Gloucester City | – | Merthyr Tydfil | | 3:2 |
| |
FA Cup 1961/62, First Qualifying Round |
| | | Gloucester City | – | Stonehouse | | 5:1 |
| |
FA Cup 1958/59, Second Qualifying Round |
| | | Lovells Athletic | – | Gloucester City | | 2:3 |
| |
FA Cup 1958/59, First Qualifying Round |
| | | Gloucester City | – | Cinderford Town | | 3:2 |
| |
FA Cup 1956/57, First Qualifying Round |
| | | Gloucester City | – | Barry Town | | 3:1 |
| |
FA Cup 1955/56, First Qualifying Round |
| | | Gloucester City | – | Ebbw Vale | | 4:1 * |
| |
FA Cup 1954/55, Second Qualifying Round |
| | | Barry Town | – | Gloucester City | | 1:4 |
| |
FA Cup 1954/55, First Qualifying Round |
| | | Cinderford Town | – | Gloucester City | | 0:3 |
| |
FA Cup 1953/54, First Qualifying Round |
| | | Gloucester City | – | Cinderford Town | | 6:1 |
| |
FA Cup 1951/52, First Qualifying Round |
| | | Stonehouse | – | Gloucester City | | 1:2 |
| |
FA Cup 1950/51, Fourth Qualifying Round |
| | | Gloucester City | – | Salisbury | | 2:1 |
| |
FA Cup 1949/50, Fourth Qualifying Round |
| | | Gloucester City | – | Bideford | | 3:1 * |
| |
FA Cup 1949/50, Third Qualifying Round |
| | | Gloucester City | – | Lovells Athletic | | 3:0 |
| |
FA Cup 1949/50, Second Qualifying Round |
| | | Gloucester City | – | Clevedon | | 3:0 |
| |
FA Cup 1949/50, First Qualifying Round |
| | | Gloucester City | – | Barry Town | | 1:0 * |
| |
FA Cup 1949/50, Preliminary Round |
| | | Weston-Super-Mare | – | Gloucester City | | 2:3 |
| |
FA Cup 1948/49, Fourth Qualifying Round |
| | | Bath City | – | Gloucester City | | 2:3 |
| |
FA Cup 1948/49, Third Qualifying Round |
| | | Gloucester City | – | Street | | 4:1 |
| |
FA Cup 1948/49, Second Qualifying Round |
| | | Gloucester City | – | Glastonbury | | 3:1 * |
| |
FA Cup 1948/49, First Qualifying Round |
| | | Gloucester City | – | Clevedon | | 8:2 |
| |
FA Cup 1948/49, Preliminary Round |
| | | Gloucester City | – | Barnstaple Town | | 5:2 |
| |
FA Cup 1948/49, Extra Preliminary Round |
| | | Gloucester City | – | Cinderford Town | | 4:0 |
| |
FA Cup 1946/47, Preliminary Round |
| | | Weston-Super-Mare St Johns | – | Gloucester City | | 0:5 |
| |
