| 1 | Sat 12 Jul | 14-2 v Sheppey SportsSheppey Sports 2-4 Sheppey United | Friendly |
| 2 | Sat 2 Aug | 13-1 v Metropolitan PoliceSheppey United 3-1 Metropolitan Police | Emirates FA Cup Extra Preliminary Round |
| 3 | Tue 19 Aug | 10-3 v Herne BayHerne Bay 3-0 Sheppey United | Kent Senior Cup |
| 4 | Sat 23 Aug | 11-1 v HassocksSheppey United 1-1 Hassocks | Isuzu FA Trophy Preliminary Round |
| 5 | Mon 25 Aug | 12-1 v SittingbourneSheppey United 2-1 Sittingbourne | Isthmian League - South East Division |
| 6 | Sat 30 Aug | 10-2 v WestfieldWestfield 2-0 Sheppey United | Emirates FA Cup First Qualifying Round |
| 7 | Tue 9 Sep | 11-7 v Three BridgesThree Bridges 7-1 Sheppey United | Isthmian League - South East Division |
| 8 | Sat 20 Sep | 11-0 v Herne BayHerne Bay 0-1 Sheppey United | Velocity Cup Second Round |
| 9 | Sat 4 Oct | 11-1 v HassocksHassocks 1-1 Sheppey United | Isthmian League - South East Division |
| 10 | Sat 11 Oct | 12-1 v Jersey BullsSheppey United 2-1 Jersey Bulls | Isthmian League - South East Division |
| 11 | Tue 14 Oct | 11-2 v Erith TownErith Town 2-1 Sheppey United | Isthmian League - South East Division |
| 12 | Sat 18 Oct | 14-5 v Broadbridge HeathBroadbridge Heath 5-4 Sheppey United | Isthmian League - South East Division |
| 13 | Tue 21 Oct | 12-0 v Beckenham TownBeckenham Town 0-2 Sheppey United | Isthmian League - South East Division |
| 14 | Sat 25 Oct | 12-0 v East Grinstead TownSheppey United 2-0 East Grinstead Town | Isthmian League - South East Division |
| 15 | Sat 1 Nov | 13-1 v Deal TownDeal Town 1-3 Sheppey United | Isthmian League - South East Division |
| 16 | Tue 4 Nov | 11-1 v Crowborough AthleticSheppey United 1-1 Crowborough Athletic | Velocity Cup Third Round |
| 17 | Tue 11 Nov | 12-0 v Herne BaySheppey United 2-0 Herne Bay | Isthmian League - South East Division |
| 18 | Sat 15 Nov | 13-1 v Crowborough AthleticCrowborough Athletic 1-3 Sheppey United | Isthmian League - South East Division |
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