FA Cup 2020/21, Second Qualifying Round |
 | 03.10.2020 |  | Christchurch | – | Gloucester City | | 1:1,
pen. 6:5 |
| Christchurch |
FA Cup 2019/20, Third Qualifying Round |
| 05.10.2019 | | Whitby Town | – | Gloucester City | | 1:1 (0:0) |
| Whitby |
FA Cup 2018/19, Third Qualifying Round |
| 06.10.2018 | | Gloucester City | – | Dorking Wanderers | | 3:3 (1:0) |
| Cheltenham |
FA Cup 2016/17, Third Qualifying Round |
| 02.10.2016 | | Gloucester City | – | Hemel Hempstead Town | | 2:2 |
| Cheltenham |
FA Cup 2014/15, Third Qualifying Round |
| 11.10.2014 | | Staines Town | – | Gloucester City | | 1:1 (0:1) |
| Staines |
FA Cup 2014/15, Second Qualifying Round |
| 27.09.2014 | | Paulton Rovers | – | Gloucester City | | 1:1 (1:0) |
| Paulton |
FA Cup 2013/14, Third Qualifying Round |
| 12.10.2013 | | Yate Town | – | Gloucester City | | 2:2 (1:0) |
| Yate |
FA Cup 2013/14, Second Qualifying Round |
| 29.09.2013 | | Gloucester City | – | Havant & Waterlooville | | 1:1 (0:0) |
| Cheltenham |
FA Cup 2011/12, Fourth Qualifying Round |
| 29.10.2011 | | Chelmsford City | – | Gloucester City | | 1:1 (0:1) |
| Chelmsford |
FA Cup 2009/10, Fourth Qualifying Round |
| 24.10.2009 | | Gloucester City | – | Lowestoft Town | | 1:1 (0:0) |
| |
FA Cup 2006/07, First Qualifying Round |
| 16.09.2006 | | Gloucester City | – | Liskeard Athletic | | 0:0 |
| |
FA Cup 2005/06, First Qualifying Round |
| 10.09.2005 | | Gloucester City | – | Christchurch | | 0:0 |
| |
FA Cup 2003/04, First Qualifying Round |
| | | Gloucester City | – | Team Bath | | 0:0 |
| |
FA Cup 2002/03, Second Qualifying Round |
| | | Gloucester City | – | Newport County |  | 1:1 |
| |
FA Cup 2000/01, Fourth Qualifying Round |
| | | Havant & Waterlooville | – | Gloucester City | | 1:1 (1:1) |
| |
FA Cup 2000/01, Second Qualifying Round |
| | | Gloucester City | – | Chippenham Town | | 1:1 |
| |
FA Cup 1999/00, Second Qualifying Round |
| | | Weymouth | – | Gloucester City | | 0:0 |
| |
FA Cup 1997/98, Fourth Qualifying Round |
| | | Gloucester City | – | Wisbech Town | | 1:1 |
| |
FA Cup 1994/95, Fourth Qualifying Round |
| | | Gloucester City | – | Worthing | | 1:1 |
| |
FA Cup 1989/90, Second Round Proper |
| 09.12.1989 | | Cardiff City | – | Gloucester City | | 2:2 |
| Cardiff |
FA Cup 1989/90, Second Qualifying Round |
| | | Barry Town | – | Gloucester City | | 2:2 |
| |
FA Cup 1986/87, Preliminary Round |
| | | Saltash United | – | Gloucester City | | 0:0 |
| |
FA Cup 1985/86, First Qualifying Round |
| | | Ton Pentre | – | Gloucester City | | 3:3 aet * |
| |
FA Cup 1985/86, First Qualifying Round |
| | | Gloucester City | – | Ton Pentre | | 0:0 |
| |
FA Cup 1977/78, First Qualifying Round |
| | | Dudley Town | – | Gloucester City | | 1:1 |
| |
FA Cup 1976/77, Preliminary Round |
| | | Gloucester City | – | Trowbridge Town | | 1:1 |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Stonehouse | – | Gloucester City | | 1:1 |
| |
FA Cup 1972/73, First Qualifying Round |
| | | Gloucester City | – | Trowbridge Town | | 2:2 |
| |
FA Cup 1969/70, First Qualifying Round |
| | | Ton Pentre | – | Gloucester City | | 2:2 |
| |
FA Cup 1968/69, Third Qualifying Round |
| | | Poole Town | – | Gloucester City | | 1:1 |
| |
FA Cup 1966/67, Second Qualifying Round |
| | | Cinderford Town | – | Gloucester City | | 2:2 |
| |
FA Cup 1965/66, Third Qualifying Round |
| | | Merthyr Tydfil | – | Gloucester City | | 1:1 aet * |
| |
FA Cup 1965/66, Third Qualifying Round |
| | | Gloucester City | – | Merthyr Tydfil | | 1:1 |
| |
FA Cup 1963/64, First Qualifying Round |
| | | Gloucester City | – | Merthyr Tydfil | | 2:2 |
| |
FA Cup 1961/62, Second Qualifying Round |
| | | Gloucester City | – | Barry Town | | 0:0 |
| |
FA Cup 1955/56, First Qualifying Round |
| | | Ebbw Vale | – | Gloucester City | | 2:2 |
| |
FA Cup 1952/53, Preliminary Round |
| | | Gloucester City | – | Llanelli | | 1:1 |
| |
FA Cup 1949/50, Fourth Qualifying Round |
| | | Bideford | – | Gloucester City | | 1:1 |
| |
FA Cup 1949/50, First Qualifying Round |
| | | Barry Town | – | Gloucester City | | 1:1 |
| |
FA Cup 1948/49, Second Qualifying Round |
| | | Glastonbury | – | Gloucester City | | 1:1 |
| |
