FA Cup 2023/24, Second Qualifying Round |
 | 16.09.2023 |  | Gloucester City | – | AFC Totton | | 0:3 (0:1) |
| Cheltenham |
FA Cup 2022/23, Third Qualifying Round |
| 01.10.2022 | | Gloucester City | – | Merthyr Town |  | 0:1 (0:0) |
| Cheltenham |
FA Cup 2021/22, Third qualifying round |
| 02.10.2021 | | Folkestone Invicta | – | Gloucester City | | 1:0 (1:0) |
| Folkestone |
FA Cup 2019/20, Third Qualifying Round |
| 07.10.2019 | | Gloucester City | – | Whitby Town | | 1:3 (0:1) * |
| Cheltenham |
FA Cup 2018/19, Fourth Qualifying Round |
| 20.10.2018 | | Gloucester City | – | Bromley | | 0:1 (0:0) |
| Cheltenham |
FA Cup 2017/18, Second Qualifying Round |
| 16.09.2017 | | Gloucester City | – | Hungerford Town | | 0:3 (0:2) |
| Cheltenham |
FA Cup 2016/17, Third Qualifying Round |
| 04.10.2016 | | Hemel Hempstead Town | – | Gloucester City | | 2:0 * |
| Hemel Hempstead |
FA Cup 2015/16, Fourth Qualifying Round |
| 24.10.2015 | | Staines Town | – | Gloucester City | | 2:1 (1:0) |
| Staines |
FA Cup 2014/15, Fourth Qualifying Round |
| 25.10.2014 | | Gloucester City | – | Forest Green Rovers | | 1:4 (1:2) |
| Cheltenham |
FA Cup 2013/14, First Round Proper |
| 09.11.2013 | | Gloucester City | – | Fleetwood Town | | 0:2 (0:1) |
| Cheltenham |
FA Cup 2012/13, First Round Proper |
| 14.11.2012 | | Gloucester City | – | Leyton Orient | | 0:2 (0:0) |
| Cheltenham |
FA Cup 2011/12, Fourth Qualifying Round |
| 01.11.2011 | | Gloucester City | – | Chelmsford City | | 0:1 (0:0) * |
| Cheltenham |
FA Cup 2010/11, Second Qualifying Round |
| 26.09.2010 | | Gloucester City | – | Weston-Super-Mare | | 0:2 |
| |
FA Cup 2009/10, Fourth Qualifying Round |
| 27.10.2009 | | Lowestoft Town | – | Gloucester City | | 4:2 * |
| |
FA Cup 2008/09, First Qualifying Round |
| 13.09.2008 | | Chalfont St Peter | – | Gloucester City | | 5:3 |
| |
FA Cup 2007/08, Second Qualifying Round |
| 30.09.2007 | | Gloucester City | – | Shortwood United | | 0:2 |
| |
FA Cup 2006/07, Second Qualifying Round |
| 30.09.2006 | | Eastleigh | – | Gloucester City | | 3:2 |
| |
FA Cup 2005/06, First Qualifying Round |
| 13.09.2005 | | Christchurch | – | Gloucester City | | 3:0 * |
| |
FA Cup 2004/05, First Qualifying Round |
| | | Street | – | Gloucester City | | 3:2 |
| |
FA Cup 2003/04, Fourth Qualifying Round |
| | | Bishop's Stortford | – | Gloucester City | | 2:0 (1:0) |
| |
FA Cup 2002/03, Second Qualifying Round |
| | | Newport County | – | Gloucester City | | 4:0 * |
| |
FA Cup 2001/02, Preliminary Round |
| | | Cirencester Town | – | Gloucester City | | 2:1 |
| |
FA Cup 2000/01, Fourth Qualifying Round |
| | | Gloucester City | – | Havant & Waterlooville | | 2:3 * |
| |
FA Cup 1999/00, Third Qualifying Round |
| | | Gloucester City | – | Merthyr Tydfil | | 2:3 |
| |
FA Cup 1998/99, Fourth Qualifying Round |
| | | Kidderminster Harriers | – | Gloucester City | | 2:1 |
| |
FA Cup 1997/98, Fourth Qualifying Round |
| | | Wisbech Town | – | Gloucester City | | 3:2 * |
| |
FA Cup 1996/97, Second Qualifying Round |
| | | Gloucester City | – | Thatcham Town | | 1:3 |
| |
FA Cup 1995/96, Second Qualifying Round |
| | | Gloucester City | – | Cinderford Town | | 0:1 |
| |
FA Cup 1994/95, Fourth Qualifying Round |
| | | Worthing | – | Gloucester City | | 2:1 * |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Gloucester City | – | Clevedon Town | | 1:2 |
| |
FA Cup 1992/93, First Qualifying Round |
| | | Gloucester City | – | Weston-Super-Mare | | 2:3 |
| |
FA Cup 1991/92, Second Qualifying Round |
| | | Worcester City | – | Gloucester City | | 2:1 |
| |
FA Cup 1990/91, Fourth Qualifying Round |
| | | Farnborough Town | – | Gloucester City | | 4:1 |
| |
FA Cup 1989/90, Second Round Proper |
| 12.12.1989 | | Gloucester City | – | Cardiff City | | 0:1 * |
| Gloucester |
FA Cup 1988/89, Third Qualifying Round |
| | | Gloucester City | – | Merthyr Tydfil | | 0:1 |
| |
FA Cup 1987/88, First Qualifying Round |
| | | Gloucester City | – | Ton Pentre | | 1:2 |
| |
FA Cup 1986/87, Preliminary Round |
| | | Gloucester City | – | Saltash United | | 0:2 * |
| |
FA Cup 1985/86, First Qualifying Round |
| | | Ton Pentre | – | Gloucester City | | 2:1 * |
| |
FA Cup 1984/85, Third Qualifying Round |
| | | Gloucester City | – | Barry Town | | 1:3 |
| |
FA Cup 1983/84, Third Qualifying Round |
| | | Merthyr Tydfil | – | Gloucester City | | 3:2 |
| |
FA Cup 1982/83, Second Qualifying Round |
| | | Cheltenham Town | – | Gloucester City | | 5:1 |
| |
FA Cup 1981/82, Second Qualifying Round |
| | | Gloucester City | – | Devizes Town | | 2:4 |
| |
FA Cup 1980/81, Second Qualifying Round |
| | | Gloucester City | – | Trowbridge Town | | 0:1 |
| |
FA Cup 1979/80, Preliminary Round |
| | | Gloucester City | – | Bridgend Town | | 0:2 |
| |
FA Cup 1978/79, First Qualifying Round |
| | | Melksham Town | – | Gloucester City | | 1:0 |
| |
FA Cup 1977/78, First Qualifying Round |
| | | Gloucester City | – | Dudley Town | | 1:2 * |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Merthyr Tydfil | – | Gloucester City | | 4:1 |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Brierley Hill Alliance | – | Gloucester City | | 2:1 |
| |
FA Cup 1974/75, Second Qualifying Round |
| | | Cheltenham Town | – | Gloucester City | | 4:1 |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Gloucester City | – | Stonehouse | | 0:1 * |
| |
FA Cup 1972/73, First Qualifying Round |
| | | Trowbridge Town | – | Gloucester City | | 2:0 * |
| |
FA Cup 1971/72, First Qualifying Round |
| | | Gloucester City | – | Merthyr Tydfil | | 2:3 |
| |
FA Cup 1970/71, First Qualifying Round |
| | | Cinderford Town | – | Gloucester City | | 3:2 |
| |
FA Cup 1969/70, First Qualifying Round |
| | | Gloucester City | – | Ton Pentre | | 0:1 * |
| |
FA Cup 1968/69, Third Qualifying Round |
| | | Gloucester City | – | Poole Town | | 1:2 * |
| |
FA Cup 1967/68, Second Qualifying Round |
| | | Gloucester City | – | Cheltenham Town | | 0:1 |
| |
FA Cup 1966/67, Second Qualifying Round |
| | | Gloucester City | – | Cinderford Town | | 0:3 * |
| |
FA Cup 1965/66, Third Qualifying Round |
| | | Gloucester City | – | Merthyr Tydfil | | 0:1 * |
| |
FA Cup 1964/65, Second Qualifying Round |
| | | Gloucester City | – | Llanelli | | 0:1 |
| |
FA Cup 1963/64, Second Qualifying Round |
| | | Gloucester City | – | Cheltenham Town | | 1:2 |
| |
FA Cup 1962/63, Third Qualifying Round |
| | | Gloucester City | – | Cheltenham Town | | 1:2 |
| |
FA Cup 1961/62, Second Qualifying Round |
| | | Barry Town | – | Gloucester City | | 2:1 * |
| |
FA Cup 1960/61, First Qualifying Round |
| | | Gloucester City | – | Cheltenham Town | | 1:4 |
| |
FA Cup 1959/60, First Qualifying Round |
| | | Gloucester City | – | Cheltenham Town | | 1:3 |
| |
FA Cup 1958/59, Third Qualifying Round |
| | | Merthyr Tydfil | – | Gloucester City | | 2:1 |
| |
FA Cup 1957/58, First Qualifying Round |
| | | Cinderford Town | – | Gloucester City | | 2:1 |
| |
FA Cup 1956/57, Second Qualifying Round |
| | | Gloucester City | – | Cheltenham Town | | 1:2 |
| |
FA Cup 1955/56, Second Qualifying Round |
| | | Barry Town | – | Gloucester City | | 5:2 |
| |
FA Cup 1954/55, Third Qualifying Round |
| | | Gloucester City | – | Merthyr Tydfil | | 0:1 |
| |
FA Cup 1953/54, Second Qualifying Round |
| | | Barry Town | – | Gloucester City | | 2:1 |
| |
FA Cup 1952/53, Preliminary Round |
| | | Llanelli | – | Gloucester City | | 5:0 * |
| |
FA Cup 1951/52, Second Qualifying Round |
| | | Gloucester City | – | Ebbw Vale | | 1:2 |
| |
FA Cup 1950/51, First Round Proper |
| 25.11.1950 | | Bristol City | – | Gloucester City | | 4:0 |
| |
FA Cup 1949/50, First Round Proper |
| 26.11.1949 | | Gloucester City | – | Norwich City | | 2:3 |
| |
FA Cup 1948/49, First Round Proper |
| 27.11.1948 | | Mansfield Town | – | Gloucester City | | 4:0 |
| |
FA Cup 1947/48, Preliminary Round |
| | | Gloucester City | – | Hanham Athletic | | 2:4 |
| |
FA Cup 1946/47, First Qualifying Round |
| | | St Philips Marsh Adult School | – | Gloucester City | | 2:0 |
| |
