FA Cup 2023/24, Third Qualifying Round |
 | 30.09.2023 | | Merthyr Town | – | Sheppey United | | 1:4 (1:1) |
| Merthyr Tydfil |
FA Cup 2023/24, Second Qualifying Round |
| 16.09.2023 | | Sheppey United | – | Burgess Hill Town | | 3:0 (1:0) |
| Isle of Sheppey |
FA Cup 2023/24, First Qualifying Round |
| 02.09.2023 | | Sheppey United | – | Kennington | | 3:1 (0:0) |
| Isle of Sheppey |
FA Cup 2023/24, Preliminary Round |
| 19.08.2023 | | Sheppey United | – | Midhurst & Easebourne | | 3:0 (1:0) |
| Isle of Sheppey |
FA Cup 2022/23, Preliminary Round |
| 23.08.2022 | | Newhaven | – | Sheppey United | | 1:2 (0:0) * |
| Newhaven |
FA Cup 2022/23, Extra Preliminary Round |
| 16.08.2022 | | Sheppey United | – | Athletic Newham | | 6:0 (2:0) * |
| Isle of Sheppey |
FA Cup 2021/22, Preliminary Round |
| 21.08.2021 | | Sheppey United | – | Saltdean United | | +:- |
| Isle of Sheppey |
FA Cup 2021/22, Extra Preliminary Round |
| 07.08.2021 | | Tower Hamlets | – | Sheppey United | | 1:4 (0:0) |
| London |
FA Cup 2020/21, Second Qualifying Round |
| 03.10.2020 | | Sheppey United | – | Welling United | | 2:0 |
| Isle of Sheppey |
FA Cup 2020/21, First Qualifying Round |
| 22.09.2020 | | Steyning Town | – | Sheppey United | | 0:5 |
| Steyning |
FA Cup 2020/21, Preliminary Round |
| 12.09.2020 | | Sheppey United | – | Uxbridge | | 4:1 |
| Isle of Sheppey |
FA Cup 2020/21, Extra Preliminary Round |
| 01.09.2020 | | Sheppey United | – | Sutton Athletic | | 1:0 |
| Isle of Sheppey |
FA Cup 2019/20, Preliminary Round |
| 24.08.2019 | | Sheppey United | – | Glebe | | 3:1 (1:0) |
| Isle of Sheppey |
FA Cup 2019/20, Extra Preliminary Round |
| 10.08.2019 | | Sheppey United | – | East Preston | | 4:1 (0:0) |
| Isle of Sheppey |
FA Cup 2017/18, Extra Preliminary Round |
| 05.08.2017 | | Sheppey United | – | AFC Croydon Athletic | | 3:2 |
| Isle of Sheppey |
FA Cup 1999/00, Preliminary Round |
| | | Wokingham Town | – | Sheppey United | | 1:4 |
| |
FA Cup 1998/99, First Qualifying Round |
| | | Lymington & New Milton | – | Sheppey United | | 1:2 * |
| |
FA Cup 1995/96, Preliminary Round |
| | | Sheppey United | – | Arundel | | 2:0 |
| |
FA Cup 1994/95, Preliminary Round |
| | | Steyning Town | – | Sheppey United | | 0:2 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Portfield | – | Sheppey United | | 0:3 * |
| |
FA Cup 1991/92, First Qualifying Round |
| | | Sheppey United | – | Hailsham Town | | 4:1 * |
| |
FA Cup 1991/92, Preliminary Round |
| | | Shoreham | – | Sheppey United | | 0:3 |
| |
FA Cup 1988/89, Preliminary Round |
| | | Maidenhead United | – | Sheppey United | | 0:1 * |
| |
FA Cup 1986/87, First Qualifying Round |
| | | Waterlooville | – | Sheppey United | | 0:1 |
| |
FA Cup 1986/87, Preliminary Round |
| | | Sheppey United | – | Chichester City | | 2:1 |
| |
FA Cup 1985/86, Preliminary Round |
| | | Fleet Town | – | Sheppey United | | 0:2 |
| |
FA Cup 1984/85, First Qualifying Round |
| | | Sheppey United | – | Whitehawk | | 2:0 |
| |
FA Cup 1982/83, Preliminary Round |
| | | Ashford Town | – | Sheppey United | | 0:2 |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Sheppey United | – | Whitstable Town | | 5:1 |
| |
FA Cup 1969/70, First Qualifying Round |
| | | Sheppey United | – | Brett Sports | | 3:1 |
| |
FA Cup 1968/69, First Qualifying Round |
| | | Herne Bay | – | Sheppey United | | 3:5 * |
| |
FA Cup 1965/66, First Qualifying Round |
| | | Cray Wanderers | – | Sheppey United | | 0:1 |
| |
FA Cup 1963/64, First Qualifying Round |
| | | Dover | – | Sheppey United | | 1:2 |
| |
FA Cup 1959/60, Preliminary Round |
| | | Chatham Town | – | Sheppey United | | 0:3 |
| |
FA Cup 1952/53, Preliminary Round |
| | | Sheppey United | – | Bowater Lloyds | | 5:1 |
| |
FA Cup 1949/50, Extra Preliminary Round |
| | | Sheppey United | – | Ashford | | 1:0 |
| |
FA Cup 1948/49, Preliminary Round |
| | | Sheppey United | – | Margate | | 5:4 |
| |
FA Cup 1947/48, Preliminary Round |
| | | Sheppey United | – | Bexley | | 3:2 |
| |
FA Cup 1946/47, Preliminary Round |
| | | Dartford | – | Sheppey United | | 2:5 |
| |
