FA Cup 1989/90, Second Round Proper |
 | 09.12.1989 |  | Maidstone United | – | Exeter City | | 1:1 |
| Dartford |
FA Cup 1988/89, Second Round Proper |
| 10.12.1988 | | Reading | – | Maidstone United | | 1:1 (1:0) |
| Reading |
FA Cup 1987/88, Second Round Proper |
| 14.12.1987 | | Kidderminster Harriers | – | Maidstone United | | 0:0 aet * |
| Kidderminster |
FA Cup 1987/88, Second Round Proper |
| 07.12.1987 | | Kidderminster Harriers | – | Maidstone United | | 2:2 aet
(1:0, 2:2) * |
| Kidderminster |
FA Cup 1987/88, Second Round Proper |
| 05.12.1987 | | Maidstone United | – | Kidderminster Harriers | | 1:1 (1:0) |
| |
FA Cup 1986/87, First Round Proper |
| 15.11.1986 | | Welling United | – | Maidstone United | | 1:1 (0:0) |
| London |
FA Cup 1986/87, Fourth Qualifying Round |
| | | Maidstone United | – | Southwick | | 2:2 aet * |
| |
FA Cup 1986/87, Fourth Qualifying Round |
| | | Maidstone United | – | Southwick | | 1:1 aet * |
| |
FA Cup 1986/87, Fourth Qualifying Round |
| | | Southwick | – | Maidstone United | | 1:1 |
| |
FA Cup 1983/84, First Round Proper |
| 19.11.1983 | | Exeter City | – | Maidstone United | | 1:1 |
| |
FA Cup 1983/84, Fourth Qualifying Round |
| | | Maidstone United | – | Sutton United | | 1:1 |
| |
FA Cup 1980/81, Second Round Proper |
| 16.12.1980 | | Maidstone United | – | Gillingham | | 0:0 aet * |
| |
FA Cup 1980/81, Second Round Proper |
| 13.12.1980 | | Gillingham | – | Maidstone United | | 0:0 |
| |
FA Cup 1980/81, First Round Proper |
| 26.11.1980 | | Maidstone United | – | Kettering Town | | 0:0 aet * |
| |
FA Cup 1980/81, First Round Proper |
| 22.11.1980 | | Kettering Town | – | Maidstone United | | 1:1 |
| |
FA Cup 1978/79, Third Round Proper |
| 09.01.1979 | | Charlton Athletic | – | Maidstone United | | 1:1 |
| |
FA Cup 1978/79, Second Qualifying Round |
| | | Dover | – | Maidstone United | | 0:0 |
| |
FA Cup 1977/78, Third Qualifying Round |
| | | Crawley Town | – | Maidstone United | | 1:1 aet * |
| |
FA Cup 1977/78, Third Qualifying Round |
| | | Maidstone United | – | Crawley Town | | 1:1 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Gravesend & Northfleet | – | Maidstone United | | 0:0 |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Ringmer | – | Maidstone United | | 1:1 |
| |
FA Cup 1974/75, First Round Proper |
| 23.11.1974 | | Nuneaton Borough | – | Maidstone United | | 2:2 |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Eastbourne Town | – | Maidstone United | | 0:0 |
| |
FA Cup 1973/74, Second Qualifying Round |
| | | Maidstone United | – | Ashford Town | | 1:1 |
| |
FA Cup 1972/73, Preliminary Round |
| | | Tonbridge | – | Maidstone United | | 1:1 |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Maidstone United | – | Eastbourne | | 2:2 |
| |
FA Cup 1962/63, First Qualifying Round |
| | | Hastings United | – | Maidstone United | | 0:0 |
| |
FA Cup 1959/60, First Qualifying Round |
| | | Tunbridge Wells United | – | Maidstone United | | 1:1 |
| |
FA Cup 1955/56, Preliminary Round |
| | | Maidstone United | – | Sheppey United | | 1:1 |
| |
FA Cup 1953/54, Preliminary Round |
| | | Sheppey United | – | Maidstone United | | 2:2 |
| |
FA Cup 1951/52, Preliminary Round |
| | | Gravesend & Northfleet | – | Maidstone United | | 2:2 |
| |
