FA Cup 2023/24, First Round Proper |
 | 03.11.2023 | | Sheppey United | – | Walsall | | 1:4 (1:1) |
| Isle of Sheppey |
FA Cup 2022/23, First Qualifying Round |
| 06.09.2022 | | Lewes | – | Sheppey United | | 8:0 (4:0) * |
| Lewes |
FA Cup 2021/22, First Qualifying Round |
| 04.09.2021 | | Sheppey United | – | Marlow | | 0:1 (0:0) |
| Isle of Sheppey |
FA Cup 2020/21, Third Qualifying Round |
| 13.10.2020 | | Eastbourne Borough | – | Sheppey United | | 3:1 |
| Eastbourne |
FA Cup 2019/20, First Qualifying Round |
| 07.09.2019 | | Chertsey Town | – | Sheppey United | | 4:1 (1:0) |
| Chertsey |
FA Cup 2018/19, Extra Preliminary Round |
| 11.08.2018 | | Cobham | – | Sheppey United | | 1:0 (0:0) |
| Cobham |
FA Cup 2017/18, Preliminary Round |
| 19.08.2017 | | Sheppey United | – | Hastings United | | 0:2 (0:0) |
| Isle of Sheppey |
FA Cup 2016/17, Extra Preliminary Round |
| 06.08.2016 | | Sheppey United | – | Badshot Lea | | 0:1 |
| |
FA Cup 2000/01, First Qualifying Round |
| | | Banstead Athletic | – | Sheppey United | | 3:1 |
| |
FA Cup 1999/00, First Qualifying Round |
| | | Corinthian-Casuals | – | Sheppey United | | 4:0 |
| |
FA Cup 1998/99, Second Qualifying Round |
| | | Leatherhead | – | Sheppey United | | 3:1 * |
| |
FA Cup 1997/98, Preliminary Round |
| | | Sheppey United | – | Windsor & Eton | | 2:3 |
| |
FA Cup 1996/97, Preliminary Round |
| | | Sheppey United | – | Harlow Town | | 1:2 |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Carshalton Athletic | – | Sheppey United | | 3:1 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | Sheppey United | – | Chertsey Town | | 0:1 |
| |
FA Cup 1993/94, Second Qualifying Round |
| | | Carshalton Athletic | – | Sheppey United | | 5:1 |
| |
FA Cup 1992/93, Preliminary Round |
| | | Sheppey United | – | Croydon | | 0:1 |
| |
FA Cup 1991/92, Second Qualifying Round |
| | | Crawley Town | – | Sheppey United | | 2:0 |
| |
FA Cup 1990/91, Preliminary Round |
| | | Sheppey United | – | Pagham | | 0:2 |
| |
FA Cup 1989/90, Preliminary Round |
| | | Egham Town | – | Sheppey United | | 4:1 |
| |
FA Cup 1988/89, First Qualifying Round |
| | | Sheppey United | – | Bromley | | 1:4 |
| |
FA Cup 1987/88, Preliminary Round |
| | | Sheppey United | – | Metropolitan Police | | 1:3 |
| |
FA Cup 1986/87, Second Qualifying Round |
| | | Newport IOW | – | Sheppey United | | 1:0 * |
| |
FA Cup 1985/86, First Qualifying Round |
| | | Sheppey United | – | Fisher Athletic | | 0:4 * |
| |
FA Cup 1984/85, Second Qualifying Round |
| | | Sheppey United | – | Hastings United | | 0:1 |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Egham Town | – | Sheppey United | | 2:1 |
| |
FA Cup 1982/83, First Qualifying Round |
| | | Welling United | – | Sheppey United | | 2:0 |
| |
FA Cup 1981/82, Preliminary Round |
| | | Sheppey United | – | Whitstable Town | | 1:2 * |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Welling United | – | Sheppey United | | 4:2 |
| |
FA Cup 1979/80, First Qualifying Round |
| | | Ramsgate | – | Sheppey United | | 5:2 * |
| |
FA Cup 1978/79, First Qualifying Round |
| | | Sheppey United | – | Canterbury City | | 1:4 |
| |
FA Cup 1977/78, Preliminary Round |
| | | Sheppey United | – | Bexhill Town | | 1:2 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Margate | – | Sheppey United | | 2:0 * |
| |
FA Cup 1975/76, Second Qualifying Round |
| | | Canterbury City | – | Sheppey United | | 6:2 |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Sheppey United | – | Dover | | 1:3 |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Sheppey United | – | Faversham Town | | 2:3 |
| |
FA Cup 1972/73, Preliminary Round |
| | | Dover | – | Sheppey United | | 1:0 * |
| |
FA Cup 1971/72, First Qualifying Round |
| | | Folkestone | – | Sheppey United | | 6:2 |
| |
FA Cup 1970/71, First Qualifying Round |
| | | Sheppey United | – | Ramsgate Athletic | | 1:2 |
| |
FA Cup 1969/70, Second Qualifying Round |
| | | Sheppey United | – | Hastings United | | 0:6 |
| |
FA Cup 1968/69, Second Qualifying Round |
| | | Sheppey United | – | Margate | | 0:6 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Deal Town | – | Sheppey United | | 2:0 |
| |
FA Cup 1965/66, Second Qualifying Round |
| | | Sheppey United | – | Bexley United | | 1:3 |
| |
FA Cup 1964/65, First Qualifying Round |
| | | Sheppey United | – | Ashford Town | | 0:1 |
| |
FA Cup 1963/64, Second Qualifying Round |
| | | Folkestone | – | Sheppey United | | 2:0 |
| |
FA Cup 1962/63, First Qualifying Round |
| | | Sheppey United | – | Dover | | 0:1 |
| |
FA Cup 1961/62, First Qualifying Round |
| | | Erith & Belvedere | – | Sheppey United | | 2:1 * |
| |
FA Cup 1960/61, First Qualifying Round |
| | | Sheppey United | – | Sittingbourne | | 1:4 |
| |
FA Cup 1959/60, First Qualifying Round |
| | | Dartford | – | Sheppey United | | 4:1 |
| |
FA Cup 1958/59, First Qualifying Round |
| | | Sheppey United | – | Gravesend & Northfleet | | 2:6 |
| |
FA Cup 1957/58, Preliminary Round |
| | | Sheppey United | – | Sittingbourne | | 2:5 |
| |
FA Cup 1956/57, Preliminary Round |
| | | Margate | – | Sheppey United | | 8:1 |
| |
FA Cup 1955/56, Preliminary Round |
| | | Sheppey United | – | Maidstone United | | 0:4 * |
| |
FA Cup 1954/55, Preliminary Round |
| | | Tonbridge | – | Sheppey United | | 6:0 |
| |
FA Cup 1953/54, Preliminary Round |
| | | Maidstone United | – | Sheppey United | | 3:1 * |
| |
FA Cup 1952/53, First Qualifying Round |
| | | Dover | – | Sheppey United | | 2:0 |
| |
FA Cup 1951/52, Preliminary Round |
| | | Sheppey United | – | Betteshanger Colliery Welfare | | 1:3 |
| |
FA Cup 1950/51, Preliminary Round |
| | | Gravesend & Northfleet | – | Sheppey United | | 5:2 |
| |
FA Cup 1949/50, Preliminary Round |
| | | Gravesend & Northfleet | – | Sheppey United | | 4:0 |
| |
FA Cup 1948/49, First Qualifying Round |
| | | Sheppey United | – | Dover | | 2:4 |
| |
FA Cup 1947/48, First Qualifying Round |
| | | Ramsgate Athletic | – | Sheppey United | | 4:2 |
| |
FA Cup 1946/47, First Qualifying Round |
| | | Sheppey United | – | Woolwich Polytechnic | | 1:3 * |
| |
FA Cup 1945/46, First Qualifying Round |
| | | Sheppey United | – | Bromley | | 1:5 |
| |
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