| 1 | Sat 9 Aug | 74-0 v Ashford UnitedSheppey United 4-0 Ashford United | Isthmian League - South East Division |
| 2 | Tue 12 Aug | 72-4 v Herne BayHerne Bay 4-2 Sheppey United | Isthmian League - South East Division |
| 3 | Mon 25 Aug | 72-1 v SittingbourneSheppey United 2-1 Sittingbourne | Isthmian League - South East Division |
| 4 | Tue 2 Sep | 71-1 v MargateSheppey United 1-1 Margate | Velocity Cup First Round |
| 5 | Tue 9 Sep | 71-7 v Three BridgesThree Bridges 7-1 Sheppey United | Isthmian League - South East Division |
| 6 | Sat 13 Sep | 70-3 v Sevenoaks TownSevenoaks Town 3-0 Sheppey United | Isthmian League - South East Division |
| 7 | Tue 16 Sep | 71-4 v Erith TownSheppey United 1-4 Erith Town | Isthmian League - South East Division |
| 8 | Sat 25 Oct | 72-0 v East Grinstead TownSheppey United 2-0 East Grinstead Town | Isthmian League - South East Division |
| 9 | Sat 1 Nov | 73-1 v Deal TownDeal Town 1-3 Sheppey United | Isthmian League - South East Division |
| 10 | Tue 4 Nov | 71-1 v Crowborough AthleticSheppey United 1-1 Crowborough Athletic | Velocity Cup Third Round |
| 11 | Tue 11 Nov | 72-0 v Herne BaySheppey United 2-0 Herne Bay | Isthmian League - South East Division |
| 12 | Sat 15 Nov | 73-1 v Crowborough AthleticCrowborough Athletic 1-3 Sheppey United | Isthmian League - South East Division |
| 13 | Sat 22 Nov | 73-3 v AFC Croydon AthleticSheppey United 3-3 AFC Croydon Athletic | Isthmian League - South East Division |
| 14 | Sat 29 Nov | 71-1 v Ashford UnitedAshford United 1-1 Sheppey United | Isthmian League - South East Division |
| 15 | Sat 6 Dec | 70-4 v AFC WhyteleafeAFC Whyteleafe 4-0 Sheppey United | Isthmian League - South East Division |
| 16 | Sat 13 Dec | 74-2 v VCD AthleticSheppey United 4-2 VCD Athletic | Isthmian League - South East Division |
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