| 1 | Sat 2 Aug | 43-1 v Metropolitan PoliceSheppey United 3-1 Metropolitan Police | Emirates FA Cup Extra Preliminary Round |
| 2 | Sat 9 Aug | 44-0 v Ashford UnitedSheppey United 4-0 Ashford United | Isthmian League - South East Division |
| 3 | Tue 12 Aug | 42-4 v Herne BayHerne Bay 4-2 Sheppey United | Isthmian League - South East Division |
| 4 | Sat 16 Aug | 49-0 v Eastbourne UnitedSheppey United 9-0 Eastbourne United | Emirates FA Cup Preliminary Round |
| 5 | Tue 19 Aug | 40-3 v Herne BayHerne Bay 3-0 Sheppey United | Kent Senior Cup |
| 6 | Sat 23 Aug | 41-1 v HassocksSheppey United 1-1 Hassocks | Isuzu FA Trophy Preliminary Round |
| 7 | Mon 25 Aug | 42-1 v SittingbourneSheppey United 2-1 Sittingbourne | Isthmian League - South East Division |
| 8 | Sat 30 Aug | 40-2 v WestfieldWestfield 2-0 Sheppey United | Emirates FA Cup First Qualifying Round |
| 9 | Tue 2 Sep | 41-1 v MargateSheppey United 1-1 Margate | Velocity Cup First Round |
| 10 | Tue 9 Sep | 41-7 v Three BridgesThree Bridges 7-1 Sheppey United | Isthmian League - South East Division |
| 11 | Sat 13 Sep | 40-3 v Sevenoaks TownSevenoaks Town 3-0 Sheppey United | Isthmian League - South East Division |
| 12 | Tue 16 Sep | 41-4 v Erith TownSheppey United 1-4 Erith Town | Isthmian League - South East Division |
| 13 | Sat 20 Sep | 41-0 v Herne BayHerne Bay 0-1 Sheppey United | Velocity Cup Second Round |
| 14 | Tue 30 Sep | 40-3 v Hastings UnitedSheppey United 0-3 Hastings United | Isthmian League - South East Division |
| 15 | Sat 11 Oct | 42-1 v Jersey BullsSheppey United 2-1 Jersey Bulls | Isthmian League - South East Division |
| 16 | Tue 14 Oct | 41-2 v Erith TownErith Town 2-1 Sheppey United | Isthmian League - South East Division |
| 17 | Tue 21 Oct | 42-0 v Beckenham TownBeckenham Town 0-2 Sheppey United | Isthmian League - South East Division |
| 18 | Sat 25 Oct | 42-0 v East Grinstead TownSheppey United 2-0 East Grinstead Town | Isthmian League - South East Division |
| 19 | Sat 1 Nov | 43-1 v Deal TownDeal Town 1-3 Sheppey United | Isthmian League - South East Division |
| 20 | Tue 4 Nov | 41-1 v Crowborough AthleticSheppey United 1-1 Crowborough Athletic | Velocity Cup Third Round |
| 21 | Sat 8 Nov | 41-1 v MersthamSheppey United 1-1 Merstham | Isthmian League - South East Division |
| 22 | Sat 15 Nov | 43-1 v Crowborough AthleticCrowborough Athletic 1-3 Sheppey United | Isthmian League - South East Division |
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