| 1 | Sat 9 Aug | 24-0 v Ashford UnitedSheppey United 4-0 Ashford United | Isthmian League - South East Division |
| 2 | Mon 25 Aug | 22-1 v SittingbourneSheppey United 2-1 Sittingbourne | Isthmian League - South East Division |
| 3 | Tue 2 Sep | 21-1 v MargateSheppey United 1-1 Margate | Velocity Cup First Round |
| 4 | Tue 9 Sep | 2 1-7 v Three BridgesThree Bridges 7-1 Sheppey United | Isthmian League - South East Division |
| 5 | Sat 20 Sep | 21-0 v Herne BayHerne Bay 0-1 Sheppey United | Velocity Cup Second Round |
| 6 | Sat 27 Sep | 22-1 v MargateSheppey United 2-1 Margate | Isthmian League - South East Division |
| 7 | Tue 30 Sep | 2 0-3 v Hastings UnitedSheppey United 0-3 Hastings United | Isthmian League - South East Division |
| 8 | Sat 4 Oct | 21-1 v HassocksHassocks 1-1 Sheppey United | Isthmian League - South East Division |
| 9 | Sat 11 Oct | 22-1 v Jersey BullsSheppey United 2-1 Jersey Bulls | Isthmian League - South East Division |
| 10 | Tue 14 Oct | 21-2 v Erith TownErith Town 2-1 Sheppey United | Isthmian League - South East Division |
| 11 | Sat 18 Oct | 24-5 v Broadbridge HeathBroadbridge Heath 5-4 Sheppey United | Isthmian League - South East Division |
| 12 | Tue 21 Oct | 22-0 v Beckenham TownBeckenham Town 0-2 Sheppey United | Isthmian League - South East Division |
| 13 | Sat 25 Oct | 2 2-0 v East Grinstead TownSheppey United 2-0 East Grinstead Town | Isthmian League - South East Division |
| 14 | Sat 1 Nov | 2 3-1 v Deal TownDeal Town 1-3 Sheppey United | Isthmian League - South East Division |
| 15 | Tue 4 Nov | 21-1 v Crowborough AthleticSheppey United 1-1 Crowborough Athletic | Velocity Cup Third Round |
| 16 | Sat 8 Nov | 21-1 v MersthamSheppey United 1-1 Merstham | Isthmian League - South East Division |
| 17 | Tue 11 Nov | 22-0 v Herne BaySheppey United 2-0 Herne Bay | Isthmian League - South East Division |
| 18 | Sat 29 Nov | 2 1-1 v Ashford UnitedAshford United 1-1 Sheppey United | Isthmian League - South East Division |
| 19 | Sat 13 Dec | 24-2 v VCD AthleticSheppey United 4-2 VCD Athletic | Isthmian League - South East Division |
| 20 | Sat 20 Dec | 22-3 v Hastings UnitedHastings United 3-2 Sheppey United | Isthmian League - South East Division |
| 21 | Sat 27 Dec | 21-2 v Faversham TownSheppey United 1-2 Faversham Town | Isthmian League - South East Division |
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