FA Cup 1991/92, First Round Proper |
 | 16.11.1991 |  | Maidstone United | – | Sutton United | | 1:0 |
| Dartford |
FA Cup 1990/91, First Round Proper |
| 17.11.1990 | | Maidstone United | – | Torquay United | | 4:1 |
| Dartford |
FA Cup 1989/90, First Round Proper |
| 19.11.1989 | | Maidstone United | – | Yeovil Town | | 2:1 |
| Dartford |
FA Cup 1988/89, First Round Proper |
| 19.11.1988 |  | Newport County | – | Maidstone United | | 1:2 (0:0) |
| Newport |
FA Cup 1987/88, Second Round Proper |
| 16.12.1987 | | Maidstone United | – | Kidderminster Harriers | | 2:1 (0:0) * |
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FA Cup 1987/88, First Round Proper |
| 14.11.1987 | | Dagenham | – | Maidstone United | | 0:2 (0:1) |
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FA Cup 1987/88, Fourth Qualifying Round |
| | | Maidstone United | – | Dartford | | 2:0 |
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FA Cup 1986/87, Second Round Proper |
| 07.12.1986 | | Maidstone United | – | Cambridge United | | 1:0 (0:0) |
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FA Cup 1986/87, First Round Proper |
| 24.11.1986 | | Maidstone United | – | Welling United | | 4:1 (2:1) * |
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FA Cup 1986/87, Fourth Qualifying Round |
| | | Southwick | – | Maidstone United | | 1:5 * |
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FA Cup 1985/86, First Round Proper |
| 16.11.1985 | | Fareham Town | – | Maidstone United | | 0:3 |
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FA Cup 1985/86, Fourth Qualifying Round |
| | | Bromley | – | Maidstone United | | 0:2 |
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FA Cup 1983/84, Second Round Proper |
| 10.12.1983 | | Maidstone United | – | Worcester City | | 3:2 |
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FA Cup 1983/84, First Round Proper |
| 23.11.1983 | | Maidstone United | – | Exeter City | | 2:1 * |
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FA Cup 1983/84, Fourth Qualifying Round |
| | | Sutton United | – | Maidstone United | | 1:3 * |
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FA Cup 1982/83, Fourth Qualifying Round |
| | | Gravesend & Northfleet | – | Maidstone United | | 1:2 |
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FA Cup 1980/81, Second Round Proper |
| 22.12.1980 | | Gillingham | – | Maidstone United | | 0:2 * |
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FA Cup 1980/81, First Round Proper |
| 01.12.1980 | | Maidstone United | – | Kettering Town | | 3:1 * |
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FA Cup 1980/81, Fourth Qualifying Round |
| | | Maidstone United | – | Barking | | 2:0 |
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FA Cup 1980/81, Third Qualifying Round |
| | | Maidstone United | – | Bromley | | 2:0 |
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FA Cup 1980/81, Second Qualifying Round |
| | | Folkestone | – | Maidstone United | | 0:2 |
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FA Cup 1980/81, First Qualifying Round |
| | | Maidstone United | – | Ramsgate | | 6:0 |
| |
FA Cup 1978/79, Second Round Proper |
| 16.12.1978 | | Maidstone United | – | Exeter City | | 1:0 |
| |
FA Cup 1978/79, First Round Proper |
| 25.11.1978 | | Maidstone United | – | Wycombe Wanderers | | 1:0 |
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FA Cup 1978/79, Fourth Qualifying Round |
| | | Waterlooville | – | Maidstone United | | 1:2 |
| |
FA Cup 1978/79, Third Qualifying Round |
| | | Ramsgate | – | Maidstone United | | 1:3 |
| |
FA Cup 1978/79, Second Qualifying Round |
| | | Maidstone United | – | Dover | | 1:0 * |
| |
FA Cup 1978/79, First Qualifying Round |
| | | Maidstone United | – | Horsham YMCA | | 2:0 |
| |
FA Cup 1977/78, Third Qualifying Round |
| | | Crawley Town | – | Maidstone United | | 1:4 * |
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FA Cup 1977/78, Second Qualifying Round |
| | | Maidstone United | – | Burgess Hill Town | | 5:0 |
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FA Cup 1977/78, First Qualifying Round |
| | | Dover | – | Maidstone United | | 0:1 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Maidstone United | – | Gravesend & Northfleet | | 3:1 * |
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FA Cup 1975/76, First Qualifying Round |
| | | Maidstone United | – | Ringmer | | 3:1 * |
| |
FA Cup 1975/76, Preliminary Round |
| | | Maidstone United | – | Eastbourne United | | 5:0 |
| |
FA Cup 1974/75, First Round Proper |
| 26.11.1974 | | Maidstone United | – | Nuneaton Borough | | 2:0 * |
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FA Cup 1974/75, Fourth Qualifying Round |
| | | Hendon | – | Maidstone United | | 0:2 |
| |
FA Cup 1974/75, Third Qualifying Round |
| | | Maidstone United | – | Medway | | 7:0 |
| |
FA Cup 1974/75, Second Qualifying Round |
| | | Maidstone United | – | Hastings United | | 6:0 |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Maidstone United | – | Eastbourne Town | | 5:3 * |
| |
FA Cup 1973/74, Third Qualifying Round |
| | | Maidstone United | – | Ramsgate | | 3:1 |
| |
FA Cup 1973/74, Second Qualifying Round |
| | | Ashford Town | – | Maidstone United | | 0:2 * |
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FA Cup 1973/74, First Qualifying Round |
| | | Maidstone United | – | Canterbury City | | 4:2 |
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FA Cup 1971/72, Second Qualifying Round |
| | | Maidstone United | – | Herne Bay | | 3:0 |
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FA Cup 1971/72, First Qualifying Round |
| | | Maidstone United | – | Tunbridge Wells | | 6:1 |
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FA Cup 1970/71, First Qualifying Round |
| | | Sittingbourne | – | Maidstone United | | 0:5 |
| |
FA Cup 1969/70, First Qualifying Round |
| | | Maidstone United | – | Tonbridge | | 5:4 |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Eastbourne | – | Maidstone United | | 1:3 * |
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FA Cup 1965/66, First Qualifying Round |
| | | Maidstone United | – | Bexhill Town | | 4:0 |
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FA Cup 1963/64, Second Qualifying Round |
| | | Tunbridge Wells United | – | Maidstone United | | 1:3 |
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FA Cup 1963/64, First Qualifying Round |
| | | Maidstone United | – | Bexhill Town | | 1:0 |
| |
FA Cup 1962/63, Third Qualifying Round |
| | | Tunbridge Wells United | – | Maidstone United | | 0:1 |
| |
FA Cup 1962/63, Second Qualifying Round |
| | | Maidstone United | – | Bexhill Town | | 5:0 |
| |
FA Cup 1962/63, First Qualifying Round |
| | | Maidstone United | – | Hastings United | | 4:2 * |
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FA Cup 1960/61, First Qualifying Round |
| | | Maidstone United | – | Gravesend & Northfleet | | 2:1 |
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FA Cup 1955/56, First Qualifying Round |
| | | Tonbridge | – | Maidstone United | | 0:1 |
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FA Cup 1955/56, Preliminary Round |
| | | Sheppey United | – | Maidstone United | | 0:4 * |
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FA Cup 1953/54, Preliminary Round |
| | | Maidstone United | – | Sheppey United | | 3:1 * |
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FA Cup 1950/51, Preliminary Round |
| | | Maidstone United | – | Ramsgate Athletic | | 5:2 |
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FA Cup 1946/47, Preliminary Round |
| | | Maidstone United | – | Margate | | 3:1 |
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