| Redhill | | 1997 | | First Round | 28-09-1997 | | Redhill | Tottenham Hotspur | 2-8 | | 1998 | | First Round | 27-09-1998 | | Chelmsford City | Redhill | W/O | |
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| 2001 | | Second Qualifying Round | 30-09-2001 | | Newport Pagnell Town | Redhill | 0-10 | | First Round | 28-10-2001 | | Denham United | Redhill | 2-4 | | Second Round | 11-11-2001 | | Redhill | Gillingham | 4-1 | | Third Round | 09-12-2001 | | Redhill | Berkhamsted Town | 4-0 | | Fourth Round | 13-01-2002 | | Garswood Saints | Redhill | 5-0 | | 2002 | | First Qualifying Round | 08-09-2002 | | Tottenham Hotspur | Redhill | 2-2 | |
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| 2003 | | First Qualifying Round | 07-09-2003 | | Aylesbury United | Redhill | 1-0 | | 2004 | | First Qualifying Round | 05-09-2004 | | Redhill | Hitchin Town | 4-0 | | Second Qualifying Round | 26-09-2004 | | Redhill | Hampton & Richmond Borough | 5-2 | | First Round | 31-10-2004 | | Redhill | Chesham United | 0-5 |
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