Hastings Town | 1996 | First Round | 29-09-1996 | | Hastings Town | Harlequins | 1-6 | 1997 | First Round | 28-09-1997 | | Teynham Gunners | Hastings Town | 4-2 | 1998 | First Round | 27-09-1998 | | Hassocks | Hastings Town | 6-0 | 1999 | Extra Preliminary Round | 12-09-1999 | | Stanway | Hastings Town | 2-1 | 2000 | Extra Preliminary Round | 10-09-2000 | | Viking Rangers | Hastings Town | 6-6 | Preliminary Round | 24-09-2000 | | Tottenham Hotspur | Hastings Town | 2-1 | |
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2001 | Second Qualifying Round | 30-09-2001 | | Hastings Town | Crowborough Athletic | 2-3 | 2002 | First Qualifying Round | 08-09-2002 | | Hastings Town | Royston Town | 0-0 | Second Qualifying Round | 29-09-2002 | | Hastings Town | Crystal Palace | 1-5 | |
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2003 | First Qualifying Round | 07-09-2003 | | Dynamo North London | Hastings Town | 3-3 | |
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Hastings United | 2004 | First Qualifying Round | 05-09-2004 | | Luton Borough | Hastings United | O-W | Second Qualifying Round | 26-09-2004 | | Hastings United | Tottenham Hotspur | 1-3 | |
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2005 | First Qualifying Round | 11-09-2005 | | Hastings United | Leighton Linslade | W/O | Second Qualifying Round | 25-09-2005 | | Hastings United | Dover Athletic | 9-2 | First Round | 23-10-2005 | | Billericay Town | Hastings United | 1-6 | Second Round | 13-11-2005 | | Leyton Orient | Hastings United | 5-3 | |
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2020 | Extra Preliminary Round | 06-09-2020 | | Hastings United | Hackney | 0-2 | 2021 | First Qualifying Round | 12-09-2021 | | Hastings United | Regents Park Rangers | 9-0 | Second Qualifying Round | 03-10-2021 | | Islington Borough | Hastings United | 1-2 | Third Qualifying Round | 24-10-2021 | | Bromley | Hastings United | 2-0 | 2022 | First Qualifying Round | 18-09-2022 | | Hastings United | Margate | W/O | Second Qualifying Round | 02-10-2022 | | Hastings United | Haringey Borough | 2-1 | Third Qualifying Round | 23-10-2022 | | Moneyfields | Hastings United | 2-0 | 2023 | First Qualifying Round | 10-09-2023 | | Camden Town | Hastings United | 3-2 |
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