| 1 | Sat 12 Aug | 82-2 v Broadbridge HeathBroadbridge Heath 2-2 Sheppey United | Isthmian League - South East Division |
| 2 | Sat 19 Aug | 83-0 v Midhurst & EasebourneSheppey United 3-0 Midhurst & Easebourne | Emirates FA Cup Preliminary Round |
| 3 | Mon 28 Aug | 8 2-2 v SittingbourneSittingbourne 2-2 Sheppey United | Isthmian League - South East Division |
| 4 | Sat 9 Sep | 81-0 v East Grinstead TownEast Grinstead Town 0-1 Sheppey United | Isuzu FA Trophy First Qualifying Round |
| 5 | Sat 16 Sep | 83-0 v Burgess Hill TownSheppey United 3-0 Burgess Hill Town | Emirates FA Cup Second Qualifying Round |
| 6 | Tue 19 Sep | 81-2 v Herne BaySheppey United 1-2 Herne Bay | Velocity Cup Second Round |
| 7 | Sat 23 Sep | 82-1 v SittingbourneSheppey United 2-1 Sittingbourne | Isuzu FA Trophy Second Qualifying Round |
| 8 | Sat 30 Sep | 84-1 v Merthyr TownMerthyr Town 1-4 Sheppey United | Emirates FA Cup Third Qualifying Round |
| 9 | Sat 7 Oct | 8 1-4 v RamsgateRamsgate 4-1 Sheppey United | Isuzu FA Trophy Third Qualifying Round |
| 10 | Sat 14 Oct | 81-1 v Billericay TownBillericay Town 1-1 Sheppey United | Emirates FA Cup Fourth Qualifying Round |
| 11 | Tue 17 Oct | 81-1 v Billericay TownSheppey United 1-1 Billericay Town | Emirates FA Cup Fourth Qualifying Round Replay |
| 12 | Sat 21 Oct | 82-3 v HorndeanSheppey United 2-3 Horndean | Isthmian League - South East Division |
| 13 | Tue 24 Oct | 83-0 v LancingSheppey United 3-0 Lancing | Isthmian League - South East Division |
| 14 | Fri 3 Nov | 81-4 v WalsallSheppey United 1-4 Walsall | Emirates FA Cup First Round |
| 15 | Tue 7 Nov | 82-0 v Beckenham TownSheppey United 2-0 Beckenham Town | Isthmian League - South East Division |
| 16 | Sat 18 Nov | 82-3 v Ashford UnitedAshford United 3-2 Sheppey United | Isthmian League - South East Division |
| 17 | Sat 25 Nov | 82-2 v Herne BaySheppey United 2-2 Herne Bay | Isthmian League - South East Division |
| 18 | Sat 2 Dec | 84-0 v Erith & BelvedereErith & Belvedere 0-4 Sheppey United | Isthmian League - South East Division |
| 19 | Tue 5 Dec | 80-0 v Burgess Hill TownSheppey United 0-0 Burgess Hill Town | Isthmian League - South East Division |
| 20 | Sat 9 Dec | 83-0 v East Grinstead TownSheppey United 3-0 East Grinstead Town | Isthmian League - South East Division |
| 21 | Tue 12 Dec | 86-0 v Littlehampton TownLittlehampton Town 0-6 Sheppey United | Isthmian League - South East Division |
| 22 | Sat 16 Dec | 82-1 v LancingLancing 1-2 Sheppey United | Isthmian League - South East Division |
| 23 | Tue 26 Dec | 83-3 v SittingbourneSheppey United 3-3 Sittingbourne | Isthmian League - South East Division |
| 24 | Sat 30 Dec | 8 1-0 v Broadbridge HeathSheppey United 1-0 Broadbridge Heath | Isthmian League - South East Division |
| 25 | Mon 1 Jan | 82-2 v Hythe TownHythe Town 2-2 Sheppey United | Isthmian League - South East Division |
| 26 | Sat 6 Jan | 81-3 v Chichester CitySheppey United 1-3 Chichester City | Isthmian League - South East Division |
| 27 | Sat 13 Jan | 81-3 v Cray Valley PMCray Valley PM 3-1 Sheppey United | Isthmian League - South East Division |
| 28 | Sat 27 Jan | 80-0 v RamsgateRamsgate 0-0 Sheppey United | Isthmian League - South East Division |
| 29 | Sat 3 Feb | 8 1-0 v Three BridgesSheppey United 1-0 Three Bridges | Isthmian League - South East Division |
| 30 | Sat 24 Feb | 80-1 v MersthamSheppey United 0-1 Merstham | Isthmian League - South East Division |
| 31 | Sat 9 Mar | 83-4 v Sevenoaks TownSheppey United 3-4 Sevenoaks Town | Isthmian League - South East Division |
| 32 | Sat 16 Mar | 80-2 v Cray Valley PMSheppey United 0-2 Cray Valley PM | Isthmian League - South East Division |
| 33 | Sat 23 Mar | 8 0-2 v Chichester CityChichester City 2-0 Sheppey United | Isthmian League - South East Division |
| 34 | Sat 30 Mar | 81-3 v Phoenix SportsPhoenix Sports 3-1 Sheppey United | Isthmian League - South East Division |
| 35 | Mon 1 Apr | 8 3-0 v Hythe TownSheppey United 3-0 Hythe Town | Isthmian League - South East Division |
| 36 | Sat 6 Apr | 85-1 v Ashford UnitedSheppey United 5-1 Ashford United | Isthmian League - South East Division |
| 37 | Tue 9 Apr | 8 2-4 v Beckenham TownBeckenham Town 4-2 Sheppey United | Isthmian League - South East Division |
| 38 | Thu 11 Apr | 85-2 v HorndeanHorndean 2-5 Sheppey United | Isthmian League - South East Division |
| 39 | Sat 13 Apr | 8 2-1 v Herne BayHerne Bay 1-2 Sheppey United | Isthmian League - South East Division |
| 40 | Tue 16 Apr | 82-1 v Burgess Hill TownBurgess Hill Town 1-2 Sheppey United | Isthmian League - South East Division |
| 41 | Sat 20 Apr | 83-0 v Erith & BelvedereSheppey United 3-0 Erith & Belvedere | Isthmian League - South East Division |
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