| 1 | Sat 15 Aug | 14-0 v Horley TownHorley Town 0-4 Sheppey United | Isthmian League - South East Division |
| 2 | Tue 18 Aug | 10-1 v MargateSheppey United 0-1 Margate | Isthmian League - South East Division |
| 3 | Tue 25 Aug | 10-3 v Herne BaySheppey United 0-3 Herne Bay | Isthmian League - South East Division |
| 4 | Tue 22 Sep | 13-0 v Punjab UnitedPunjab United 0-3 Sheppey United | Isthmian League - South East Division |
| 5 | Sat 26 Sep | 12-1 v Peacehaven & TelscombeSheppey United 2-1 Peacehaven & Telscombe | Isthmian League - South East Division |
| 6 | Tue 29 Sep | 11-1 v Herne BaySheppey United 1-1 Herne Bay | Velocity Cup Second Round |
| 7 | Sat 3 Oct | 10-2 v Chertsey TownSheppey United 0-2 Chertsey Town | Emirates FA Cup Third Qualifying Round |
| 8 | Sat 10 Oct | 11-2 v Hastings UnitedSheppey United 1-2 Hastings United | Isthmian League - South East Division |
| 9 | Tue 13 Oct | 11-1 v Broadbridge HeathSheppey United 1-1 Broadbridge Heath | Isthmian League - South East Division |
| 10 | Sat 17 Oct | 12-1 v Steyning TownSteyning Town 1-2 Sheppey United | Isthmian League - South East Division |
| 11 | Tue 20 Oct | 11-2 v MargateMargate 2-1 Sheppey United | Isthmian League - South East Division |
| 12 | Sat 24 Oct | 11-0 v Horley TownSheppey United 1-0 Horley Town | Isthmian League - South East Division |
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