FA Cup 2023/24, Fourth Qualifying Round |
 | 17.10.2023 |  | Sheppey United | – | Billericay Town | | 1:1 aet
(1:0, 1:1),
pen. 5:4 * |
| Isle of Sheppey |
FA Cup 2023/24, Fourth Qualifying Round |
| 14.10.2023 | | Billericay Town | – | Sheppey United | | 1:1 (1:1) |
| Billericay |
FA Cup 2022/23, First Qualifying Round |
| 03.09.2022 | | Sheppey United | – | Lewes | | 2:2 (1:0) |
| Isle of Sheppey |
FA Cup 2022/23, Preliminary Round |
| 20.08.2022 | | Sheppey United | – | Newhaven | | 0:0 |
| Isle of Sheppey |
FA Cup 2022/23, Extra Preliminary Round |
| 09.08.2022 | | Athletic Newham | – | Sheppey United | | 3:3 (1:1) |
| Isle of Sheppey |
FA Cup 2000/01, Preliminary Round |
| | | Sheppey United | – | BAT Sports | | 2:2,
pen. 5:4 * |
| |
FA Cup 2000/01, Preliminary Round |
| | | BAT Sports | – | Sheppey United | | 0:0 |
| |
FA Cup 1998/99, Second Qualifying Round |
| | | Sheppey United | – | Leatherhead | | 0:0 |
| |
FA Cup 1998/99, First Qualifying Round |
| | | Sheppey United | – | Lymington & New Milton | | 0:0 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Sheppey United | – | Portfield | | 1:1 |
| |
FA Cup 1991/92, First Qualifying Round |
| | | Hailsham Town | – | Sheppey United | | 1:1 |
| |
FA Cup 1988/89, Preliminary Round |
| | | Sheppey United | – | Maidenhead United | | 1:1 |
| |
FA Cup 1986/87, Second Qualifying Round |
| | | Sheppey United | – | Newport IOW | | 1:1 |
| |
FA Cup 1985/86, First Qualifying Round |
| | | Fisher Athletic | – | Sheppey United | | 2:2 aet * |
| |
FA Cup 1985/86, First Qualifying Round |
| | | Sheppey United | – | Fisher Athletic | | 1:1 |
| |
FA Cup 1981/82, Preliminary Round |
| | | Whitstable Town | – | Sheppey United | | 2:2 |
| |
FA Cup 1979/80, First Qualifying Round |
| | | Sheppey United | – | Ramsgate | | 1:1 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Sheppey United | – | Margate | | 2:2 |
| |
FA Cup 1972/73, Preliminary Round |
| | | Sheppey United | – | Dover | | 2:2 |
| |
FA Cup 1968/69, First Qualifying Round |
| | | Sheppey United | – | Herne Bay | | 1:1 |
| |
FA Cup 1961/62, First Qualifying Round |
| | | Sheppey United | – | Erith & Belvedere | | 2:2 |
| |
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 1946/47, First Qualifying Round |
| | | Woolwich Polytechnic | – | Sheppey United | | 0:0 |
| |
