| 1 | Sat 26 Aug | 173-0 v HorndeanHorndean 0-3 Sittingbourne | Isthmian League - South East Division |
| 2 | Mon 28 Aug | 10 2-2 v Sheppey UnitedSittingbourne 2-2 Sheppey United | Isthmian League - South East Division |
| 3 | Sat 2 Sep | 92-1 v Ashford UnitedSittingbourne 2-1 Ashford United | Kent Senior Cup First Round |
| 4 | Sat 9 Sep | 92-1 v Ashford Town (Middx)Sittingbourne 2-1 Ashford Town (Middx) | Isuzu FA Trophy First Qualifying Round |
| 5 | Sat 16 Sep | 141-0 v MersthamMerstham 0-1 Sittingbourne | Isthmian League - South East Division |
| 6 | Tue 19 Sep | 9 1-1 v Hythe TownSittingbourne 1-1 Hythe Town | Velocity Cup Second Round |
| 7 | Sat 23 Sep | 9 1-2 v Sheppey UnitedSheppey United 2-1 Sittingbourne | Isuzu FA Trophy Second Qualifying Round |
| 8 | Sat 30 Sep | 72-2 v Sevenoaks TownSevenoaks Town 2-2 Sittingbourne | Isthmian League - South East Division |
| 9 | Sat 7 Oct | 76-0 v Erith & BelvedereSittingbourne 6-0 Erith & Belvedere | Isthmian League - South East Division |
| 10 | Tue 10 Oct | 72-0 v Herne BaySittingbourne 2-0 Herne Bay | Isthmian League - South East Division |
| 11 | Sat 14 Oct | 16 1-1 v Burgess Hill TownBurgess Hill Town 1-1 Sittingbourne | Isthmian League - South East Division |
| 12 | Sat 11 Nov | 151-0 v Ashford UnitedSittingbourne 1-0 Ashford United | Isthmian League - South East Division |
| 13 | Tue 21 Nov | 100-6 v Three BridgesThree Bridges 6-0 Sheppey United | Isthmian League - South East Division |
| 14 | Sat 25 Nov | 102-2 v Herne BaySheppey United 2-2 Herne Bay | Isthmian League - South East Division |
| 15 | Sat 2 Dec | 104-0 v Erith & BelvedereErith & Belvedere 0-4 Sheppey United | Isthmian League - South East Division |
| 16 | Tue 5 Dec | 100-0 v Burgess Hill TownSheppey United 0-0 Burgess Hill Town | Isthmian League - South East Division |
| 17 | Sat 9 Dec | 10 3-0 v East Grinstead TownSheppey United 3-0 East Grinstead Town | Isthmian League - South East Division |
| 18 | Tue 12 Dec | 106-0 v Littlehampton TownLittlehampton Town 0-6 Sheppey United | Isthmian League - South East Division |
| 19 | Sat 16 Dec | 102-1 v LancingLancing 1-2 Sheppey United | Isthmian League - South East Division |
| 20 | Tue 26 Dec | 103-3 v SittingbourneSheppey United 3-3 Sittingbourne | Isthmian League - South East Division |
| 21 | Sat 30 Dec | 101-0 v Broadbridge HeathSheppey United 1-0 Broadbridge Heath | Isthmian League - South East Division |
| 22 | Mon 1 Jan | 102-2 v Hythe TownHythe Town 2-2 Sheppey United | Isthmian League - South East Division |
| 23 | Sat 6 Jan | 10 1-3 v Chichester CitySheppey United 1-3 Chichester City | Isthmian League - South East Division |
| 24 | Sat 13 Jan | 101-3 v Cray Valley PMCray Valley PM 3-1 Sheppey United | Isthmian League - South East Division |
| 25 | Sat 20 Jan | 102-1 v Littlehampton TownSheppey United 2-1 Littlehampton Town | Isthmian League - South East Division |
| 26 | Sat 27 Jan | 100-0 v RamsgateRamsgate 0-0 Sheppey United | Isthmian League - South East Division |
| 27 | Sat 3 Feb | 101-0 v Three BridgesSheppey United 1-0 Three Bridges | Isthmian League - South East Division |
| 28 | Sat 24 Feb | 100-1 v MersthamSheppey United 0-1 Merstham | Isthmian League - South East Division |
| 29 | Sat 9 Mar | 103-4 v Sevenoaks TownSheppey United 3-4 Sevenoaks Town | Isthmian League - South East Division |
| 30 | Sat 27 Apr | 10 2-1 v East Grinstead TownEast Grinstead Town 1-2 Sheppey United | Isthmian League - South East Division |
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