| Gloucester City |  | | 2003 | | Second Qualifying Round | 28-09-2003 | | Alphington | Gloucester City | 3-2 | | 2004 | | Second Qualifying Round | 26-09-2004 | | AFC Bournemouth | Gloucester City | 6-2 | | 2005 | | First Qualifying Round | 11-09-2005 | | Gloucester City | Alphington | 12-0 | | Second Qualifying Round | 25-09-2005 | | Gloucester City | Team Bath | 2-3 | | 2006 | | Preliminary Round | 10-09-2006 | | Yeovil Town | Gloucester City | 1-3 | | First Qualifying Round | 24-09-2006 | | Gloucester City | Launceston | 10-0 | | Second Qualifying Round | 08-10-2006 | | Gloucester City | Bath City | 4-0 | | First Round | 29-10-2006 | | Gloucester City | Newquay | 2-4 | |
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| 2007 | | First Qualifying Round | 16-09-2007 | | Gloucester City | Oxford City | 0-2 | | 2010 | | Third Qualifying Round | 14-11-2010 | | Southampton Saints | Gloucester City | 3-1 | | 2011 | | Third Qualifying Round | 13-11-2011 | | Larkhall Athletic | Gloucester City | 5-2 | |
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| 2012 | | Third Qualifying Round | 11-11-2012 | | Gloucester City | Keynsham Town | 0-5 | | 2013 | | First Qualifying Round | 22-09-2013 | | Gloucester City | Longlevens | 10-2 | | Second Qualifying Round | 06-10-2013 | | Gloucester City | Brislington | 4-1 | | Third Qualifying Round | 03-11-2013 | | Gloucester City | Southampton Saints | 1-0 | | First Round | 01-12-2013 | | Chichester City | Gloucester City | 6-0 | | 2015 | | Third Qualifying Round | 11-10-2015 | | Gloucester City | Southampton Saints | O-W | |
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| 2021 | | First Qualifying Round | 12-09-2021 | | Gloucester City | Weston Super Mare | 3-2 | | Second Qualifying Round | 03-10-2021 | | Gloucester City | Ilminster Town | 0-11 | | 2022 | | First Qualifying Round | 18-09-2022 | | Gloucester City | Bishop's Cleeve | 2-2 | |
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| 2023 | | First Qualifying Round | 10-09-2023 | | Gloucester City | Cirencester Town | 2-1 | | Second Qualifying Round | 01-10-2023 | | Gloucester City | Bath City | 2-0 | | Third Qualifying Round | 22-10-2023 | | Moneyfields | Gloucester City | 4-0 |
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