| 1 | Sat 10 Aug | 52-1 v Three BridgesThree Bridges 1-2 Sheppey United | Isthmian League - South East Division |
| 2 | Sat 17 Aug | 53-0 v North Greenford UnitedNorth Greenford United 0-3 Sheppey United | Emirates FA Cup Preliminary Round |
| 3 | Sat 31 Aug | 5 1-1 v Hanwell TownSheppey United 1-1 Hanwell Town | Emirates FA Cup First Qualifying Round |
| 4 | Tue 3 Sep | 50-6 v Hanwell TownHanwell Town 6-0 Sheppey United | Emirates FA Cup First Qualifying Round Replay |
| 5 | Sat 7 Sep | 52-3 v RamsgateSheppey United 2-3 Ramsgate | Isuzu FA Trophy First Qualifying Round |
| 6 | Tue 10 Sep | 53-1 v Erith TownSheppey United 3-1 Erith Town | Isthmian League - South East Division |
| 7 | Tue 17 Sep | 50-0 v Herne BaySheppey United 0-0 Herne Bay | Velocity Cup Second Round |
| 8 | Sat 21 Sep | 52-0 v Steyning Town CommunitySheppey United 2-0 Steyning Town Community | Isthmian League - South East Division |
| 9 | Sat 28 Sep | 52-0 v Phoenix SportsPhoenix Sports 0-2 Sheppey United | Isthmian League - South East Division |
| 10 | Sat 12 Oct | 50-5 v RamsgateRamsgate 5-0 Sheppey United | Isthmian League - South East Division |
| 11 | Tue 15 Oct | 5 1-1 v MersthamMerstham 1-1 Sheppey United | Isthmian League - South East Division |
| 12 | Sat 19 Oct | 52-3 v MargateSheppey United 2-3 Margate | Isthmian League - South East Division |
| 13 | Tue 22 Oct | 52-0 v Littlehampton TownSheppey United 2-0 Littlehampton Town | Isthmian League - South East Division |
| 14 | Sat 26 Oct | 54-0 v Herne BayHerne Bay 0-4 Sheppey United | Isthmian League - South East Division |
| 15 | Sat 2 Nov | 5 0-1 v Beckenham TownSheppey United 0-1 Beckenham Town | Isthmian League - South East Division |
| 16 | Tue 5 Nov | 51-1 v Erith TownErith Town 1-1 Sheppey United | Isthmian League - South East Division |
| 17 | Sat 9 Nov | 54-3 v MersthamSheppey United 4-3 Merstham | Isthmian League - South East Division |
| 18 | Sat 16 Nov | 50-3 v Burgess Hill TownBurgess Hill Town 3-0 Sheppey United | Isthmian League - South East Division |
| 19 | Tue 26 Nov | 54-2 v MargateMargate 2-4 Sheppey United | Velocity Cup Third Qualifying Round |
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