| Gillingham | | 1977 | | Second Round | 02-10-1977 | | Dartford College | Gillingham | 10-0 | | 1978 | | Preliminary Round | 08-10-1978 | | Teynham Strykers | Gillingham | 6-4 | | 1979 | | First Round - Group G | 28-10-1979 | | Gillingham | Thanet Bluebirds | 8-1 | | Second Round - Group G | 02-12-1979 | | Maidstone | Gillingham | W/O | |
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| 1980 | | First Round - Group B | 05-10-1980 | | Gillingham | Herne Bay | 4-3 | | Second Round - Group B | 02-11-1980 | | Southampton | Gillingham | 12-0 | | 1982 | | First Round - Group B | 10-10-1982 | | Gillingham | Hassocks Beacon | 11-1 | | Second Round - Group B | 07-11-1982 | | Reigate | Gillingham | 2-1 | | 1983 | | First Round - South East Group | 02-10-1983 | | Howbury Grange | Gillingham | 10-1 | | 1984 | | First Round - Group B | 07-10-1984 | | Reigate | Gillingham | 3-0 | | 1986 | | First Round - Group H | Bye |
| Second Round - Group H | 02-11-1986 | | Reigate | Gillingham | 4-1 | |
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| 1987 | | First Round - Group H | Bye |
| Second Round - Group H | 11-10-1987 | | Gillingham | Reigate | 0-8 | | 1988 | | First Round - Group H | 25-09-1988 | | Gillingham | Maidstone Mote United | O-W |
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