| Okeford United | | 1996 | | First Round | 29-09-1996 | | Okeford United | Bridgwater Town | 3-2 | | Second Round | 03-11-1996 | | Bath City | Okeford United | 2-2 | | Second Round | 10-11-1996 | | Okeford United | Bath City | 2-1 | | Third Round | 01-12-1996 | | Okeford United | Denham United | 1-2 | |
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| 1997 | | First Round | 28-09-1997 | | Okeford United | Slough Town | W/O | | Second Round | 02-11-1997 | | Binfield | Okeford United | 1-0 | |
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| 1998 | | First Round | 27-09-1998 | | Keynsham Town | Okeford United | 1-6 | | Second Round | 01-11-1998 | | Bristol Rovers | Okeford United | 6-0 | | 1999 | | Extra Preliminary Round | 12-09-1999 | | Elmore Eagles | Okeford United | 1-7 | | Preliminary Round | 26-09-1999 | | Dorchester | Okeford United | 2-8 | | First Round | 10-10-1999 | | Southampton | Okeford United | 0-6 | | Second Round | 07-11-1999 | | Fulham | Okeford United | 5-0 | | 2000 | | Extra Preliminary Round | 10-09-2000 | | Warminster Town | Okeford United | 0-11 | | Preliminary Round | 24-09-2000 | | Marjons | Okeford United | 0-5 | | First Round | 29-10-2000 | | Portsmouth | Okeford United | 9-2 | | 2001 | | 1st Qualifying Round | 09-09-2001 | | Okeford United | Keynsham Town | 1-4 | | 2002 | | 1st Qualifying Round | 08-09-2002 | | Alphington | Okeford United | 2-8 | | 2nd Qualifying Round | 29-09-2002 | | Launceston | Okeford United | 4-7 | | First Round | 03-11-2002 | | Cardiff City | Okeford United | 10-2 |
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