FA Cup 1991/92, Second Round Proper |
 | 07.12.1991 |  | Maidstone United | – | Kettering Town | | 1:2 |
| Dartford |
FA Cup 1990/91, Second Round Proper |
| 08.12.1990 | | Aldershot | – | Maidstone United | | 2:1 |
| Aldershot |
FA Cup 1989/90, Second Round Proper |
| 13.12.1989 | | Exeter City | – | Maidstone United | | 3:2 * |
| Exeter |
FA Cup 1988/89, Second Round Proper |
| 14.12.1988 | | Maidstone United | – | Reading | | 1:2 (0:1) * |
| Dartford |
FA Cup 1987/88, Third Round Proper |
| 09.01.1988 | | Sheffield United | – | Maidstone United | | 1:0 (0:0) |
| Sheffield |
FA Cup 1986/87, Third Round Proper |
| 10.01.1987 | | Watford | – | Maidstone United | | 3:1 (1:1) |
| Watford |
FA Cup 1985/86, Second Round Proper |
| 07.12.1985 | | Plymouth Argyle | – | Maidstone United | | 3:0 |
| |
FA Cup 1984/85, Fourth Qualifying Round |
| | | Bishop's Stortford | – | Maidstone United | | 1:0 |
| |
FA Cup 1983/84, Third Round Proper |
| 07.01.1984 | | Darlington | – | Maidstone United | | 4:1 |
| |
FA Cup 1982/83, First Round Proper |
| 20.11.1982 | | Weymouth | – | Maidstone United | | 4:3 |
| |
FA Cup 1981/82, Fourth Qualifying Round |
| | | Maidstone United | – | Barking | | 0:1 |
| |
FA Cup 1980/81, Third Round Proper |
| 03.01.1981 | | Maidstone United | – | Exeter City | | 2:4 |
| |
FA Cup 1979/80, Fourth Qualifying Round |
| | | Chesham United | – | Maidstone United | | 3:1 |
| |
FA Cup 1978/79, Third Round Proper |
| 15.01.1979 | | Maidstone United | – | Charlton Athletic | | 1:2 * |
| |
FA Cup 1977/78, Fourth Qualifying Round |
| | | Wealdstone | – | Maidstone United | | 2:1 |
| |
FA Cup 1976/77, Second Qualifying Round |
| | | Cray Wanderers | – | Maidstone United | | 2:1 |
| |
FA Cup 1975/76, Second Qualifying Round |
| | | Maidstone United | – | Ramsgate | | 1:2 |
| |
FA Cup 1974/75, Second Round Proper |
| 14.12.1974 | | Swindon Town | – | Maidstone United | | 3:1 |
| |
FA Cup 1973/74, Fourth Qualifying Round |
| | | Wimbledon | – | Maidstone United | | 1:0 |
| |
FA Cup 1972/73, Preliminary Round |
| | | Maidstone United | – | Tonbridge | | 1:2 * |
| |
FA Cup 1971/72, Third Qualifying Round |
| | | Folkestone | – | Maidstone United | | 2:0 |
| |
FA Cup 1970/71, Second Qualifying Round |
| | | Maidstone United | – | Hastings United | | 0:2 |
| |
FA Cup 1969/70, Second Qualifying Round |
| | | Ashford Town | – | Maidstone United | | 1:0 |
| |
FA Cup 1968/69, First Qualifying Round |
| | | Maidstone United | – | Ashford Town | | 1:2 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Chatham Town | – | Maidstone United | | 4:2 |
| |
FA Cup 1966/67, Second Qualifying Round |
| | | Crawley Town | – | Maidstone United | | 1:0 |
| |
FA Cup 1965/66, Second Qualifying Round |
| | | Maidstone United | – | Hastings United | | 1:5 |
| |
FA Cup 1964/65, First Qualifying Round |
| | | Maidstone United | – | Hastings United | | 1:3 |
| |
FA Cup 1963/64, Third Qualifying Round |
| | | Maidstone United | – | Tonbridge | | 1:5 |
| |
FA Cup 1962/63, Fourth Qualifying Round |
| | | Dartford | – | Maidstone United | | 2:0 |
| |
FA Cup 1961/62, First Qualifying Round |
| | | Tunbridge Wells United | – | Maidstone United | | 1:0 |
| |
FA Cup 1960/61, Second Qualifying Round |
| | | Maidstone United | – | Dartford | | 1:3 |
| |
FA Cup 1959/60, First Qualifying Round |
| | | Maidstone United | – | Tunbridge Wells United | | 2:3 * |
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FA Cup 1958/59, Preliminary Round |
| | | Tunbridge Wells United | – | Maidstone United | | 3:1 |
| |
FA Cup 1957/58, Preliminary Round |
| | | Maidstone United | – | Whitstable | | 1:3 |
| |
FA Cup 1956/57, Preliminary Round |
| | | Betteshanger Colliery Welfare | – | Maidstone United | | 1:0 |
| |
FA Cup 1955/56, Second Qualifying Round |
| | | Maidstone United | – | Margate | | 1:4 |
| |
FA Cup 1954/55, Preliminary Round |
| | | Maidstone United | – | Bromley | | 1:3 |
| |
FA Cup 1953/54, First Qualifying Round |
| | | Maidstone United | – | Margate | | 1:3 |
| |
FA Cup 1952/53, Preliminary Round |
| | | Maidstone United | – | Bromley | | 0:6 |
| |
FA Cup 1951/52, Preliminary Round |
| | | Maidstone United | – | Gravesend & Northfleet | | 0:3 * |
| |
FA Cup 1950/51, First Qualifying Round |
| | | Sittingbourne | – | Maidstone United | | 2:0 |
| |
FA Cup 1947/48, Preliminary Round |
| | | Maidstone United | – | Ramsgate Athletic | | 3:4 |
| |
FA Cup 1946/47, First Qualifying Round |
| | | Maidstone United | – | Ashford | | 3:5 |
| |
FA Cup 1992/93, First Round Proper |
| |  | Swansea City | – | Maidstone United | | +:- |
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