| 1 | Sat 17 Aug | 33-0 v North Greenford UnitedNorth Greenford United 0-3 Sheppey United | Emirates FA Cup Preliminary Round |
| 2 | Sat 24 Aug | 33-1 v Sevenoaks TownSheppey United 3-1 Sevenoaks Town | Isthmian League - South East Division |
| 3 | Mon 26 Aug | 34-0 v Hythe TownHythe Town 0-4 Sheppey United | Isthmian League - South East Division |
| 4 | Sat 31 Aug | 31-1 v Hanwell TownSheppey United 1-1 Hanwell Town | Emirates FA Cup First Qualifying Round |
| 5 | Tue 3 Sep | 30-6 v Hanwell TownHanwell Town 6-0 Sheppey United | Emirates FA Cup First Qualifying Round Replay |
| 6 | Sat 7 Sep | 32-3 v RamsgateSheppey United 2-3 Ramsgate | Isuzu FA Trophy First Qualifying Round |
| 7 | Tue 10 Sep | 33-1 v Erith TownSheppey United 3-1 Erith Town | Isthmian League - South East Division |
| 8 | Tue 17 Sep | 30-0 v Herne BaySheppey United 0-0 Herne Bay | Velocity Cup Second Round |
| 9 | Tue 24 Sep | 31-1 v Hythe TownSheppey United 1-1 Hythe Town | Kent Senior Cup First Round |
| 10 | Sat 28 Sep | 32-0 v Phoenix SportsPhoenix Sports 0-2 Sheppey United | Isthmian League - South East Division |
| 11 | Sat 12 Oct | 30-5 v RamsgateRamsgate 5-0 Sheppey United | Isthmian League - South East Division |
| 12 | Sat 26 Oct | 34-0 v Herne BayHerne Bay 0-4 Sheppey United | Isthmian League - South East Division |
| 13 | Sat 16 Nov | 30-3 v Burgess Hill TownBurgess Hill Town 3-0 Sheppey United | Isthmian League - South East Division |
| 14 | Tue 3 Dec | 33-0 v DartfordSheppey United 3-0 Dartford | Velocity Cup Fourth Round |
| 15 | Sat 7 Dec | 30-0 v LancingLancing 0-0 Sheppey United | Isthmian League - South East Division |
| 16 | Wed 1 Jan | 33-1 v Hythe TownSheppey United 3-1 Hythe Town | Isthmian League - South East Division |
| 17 | Sat 18 Jan | 33-2 v Broadbridge HeathSheppey United 3-2 Broadbridge Heath | Isthmian League - South East Division |
| 18 | Tue 21 Jan | 32-2 v Burgess Hill TownSheppey United 2-2 Burgess Hill Town | Isthmian League - South East Division |
| 19 | Sat 25 Jan | 32-2 v Eastbourne TownEastbourne Town 2-2 Sheppey United | Isthmian League - South East Division |
| 20 | Sat 1 Feb | 32-1 v LancingSheppey United 2-1 Lancing | Isthmian League - South East Division |
| 21 | Tue 4 Feb | 31-2 v AFC Croydon AthleticAFC Croydon Athletic 2-1 Sheppey United | Isthmian League - South East Division |
| 22 | Sat 8 Feb | 31-3 v Littlehampton TownLittlehampton Town 3-1 Sheppey United | Isthmian League - South East Division |
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