| 1 | Sat 9 Aug | 54-0 v Ashford UnitedSheppey United 4-0 Ashford United | Isthmian League - South East Division |
| 2 | Tue 12 Aug | 52-4 v Herne BayHerne Bay 4-2 Sheppey United | Isthmian League - South East Division |
| 3 | Mon 25 Aug | 52-1 v SittingbourneSheppey United 2-1 Sittingbourne | Isthmian League - South East Division |
| 4 | Tue 2 Sep | 51-1 v MargateSheppey United 1-1 Margate | Velocity Cup First Round |
| 5 | Tue 9 Sep | 51-7 v Three BridgesThree Bridges 7-1 Sheppey United | Isthmian League - South East Division |
| 6 | Tue 16 Sep | 5 1-4 v Erith TownSheppey United 1-4 Erith Town | Isthmian League - South East Division |
| 7 | Sat 20 Sep | 51-0 v Herne BayHerne Bay 0-1 Sheppey United | Velocity Cup Second Round |
| 8 | Sat 27 Sep | 52-1 v MargateSheppey United 2-1 Margate | Isthmian League - South East Division |
| 9 | Tue 30 Sep | 50-3 v Hastings UnitedSheppey United 0-3 Hastings United | Isthmian League - South East Division |
| 10 | Sat 4 Oct | 51-1 v HassocksHassocks 1-1 Sheppey United | Isthmian League - South East Division |
| 11 | Sat 11 Oct | 52-1 v Jersey BullsSheppey United 2-1 Jersey Bulls | Isthmian League - South East Division |
| 12 | Tue 14 Oct | 51-2 v Erith TownErith Town 2-1 Sheppey United | Isthmian League - South East Division |
| 13 | Sat 18 Oct | 54-5 v Broadbridge HeathBroadbridge Heath 5-4 Sheppey United | Isthmian League - South East Division |
| 14 | Tue 21 Oct | 52-0 v Beckenham TownBeckenham Town 0-2 Sheppey United | Isthmian League - South East Division |
| 15 | Sat 25 Oct | 52-0 v East Grinstead TownSheppey United 2-0 East Grinstead Town | Isthmian League - South East Division |
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