| 1 | Tue 15 Aug | 43-3 v Sevenoaks TownSittingbourne 3-3 Sevenoaks Town | Velocity Cup First Round |
| 2 | Sat 26 Aug | 63-0 v HorndeanHorndean 0-3 Sittingbourne | Isthmian League - South East Division |
| 3 | Mon 28 Aug | 62-2 v Sheppey UnitedSittingbourne 2-2 Sheppey United | Isthmian League - South East Division |
| 4 | Sat 2 Sep | 62-1 v Ashford UnitedSittingbourne 2-1 Ashford United | Kent Senior Cup First Round |
| 5 | Sat 9 Sep | 82-1 v Ashford Town (Middx)Sittingbourne 2-1 Ashford Town (Middx) | Isuzu FA Trophy First Qualifying Round |
| 6 | Sat 16 Sep | 81-0 v MersthamMerstham 0-1 Sittingbourne | Isthmian League - South East Division |
| 7 | Tue 19 Sep | 151-1 v Hythe TownSittingbourne 1-1 Hythe Town | Velocity Cup Second Round |
| 8 | Sat 23 Sep | 8 1-2 v Sheppey UnitedSheppey United 2-1 Sittingbourne | Isuzu FA Trophy Second Qualifying Round |
| 9 | Sat 30 Sep | 82-2 v Sevenoaks TownSevenoaks Town 2-2 Sittingbourne | Isthmian League - South East Division |
| 10 | Sat 7 Oct | 86-0 v Erith & BelvedereSittingbourne 6-0 Erith & Belvedere | Isthmian League - South East Division |
| 11 | Tue 10 Oct | 82-0 v Herne BaySittingbourne 2-0 Herne Bay | Isthmian League - South East Division |
| 12 | Sat 14 Oct | 81-1 v Burgess Hill TownBurgess Hill Town 1-1 Sittingbourne | Isthmian League - South East Division |
| 13 | Sat 11 Nov | 81-0 v Ashford UnitedSittingbourne 1-0 Ashford United | Isthmian League - South East Division |
| 14 | Sat 18 Nov | 84-1 v Three BridgesSittingbourne 4-1 Three Bridges | Isthmian League - South East Division |
| 15 | Tue 21 Nov | 82-0 v Chichester CityChichester City 0-2 Sittingbourne | Isthmian League - South East Division |
| 16 | Sat 25 Nov | 80-0 v LancingLancing 0-0 Sittingbourne | Isthmian League - South East Division |
| 17 | Tue 28 Nov | 80-1 v Hythe TownSittingbourne 0-1 Hythe Town | Isthmian League - South East Division |
| 18 | Sat 2 Dec | 102-1 v Phoenix SportsSittingbourne 2-1 Phoenix Sports | Isthmian League - South East Division |
| 19 | Sat 16 Dec | 8 3-0 v MersthamSittingbourne 3-0 Merstham | Isthmian League - South East Division |
| 20 | Tue 26 Dec | 83-3 v Sheppey UnitedSheppey United 3-3 Sittingbourne | Isthmian League - South East Division |
| 21 | Sat 30 Dec | 82-2 v Cray Valley PMCray Valley PM 2-2 Sittingbourne | Isthmian League - South East Division |
| 22 | Mon 1 Jan | 82-3 v RamsgateSittingbourne 2-3 Ramsgate | Isthmian League - South East Division |
| 23 | Sat 6 Jan | 84-0 v Beckenham TownSittingbourne 4-0 Beckenham Town | Isthmian League - South East Division |
| 24 | Sat 13 Jan | 82-0 v Broadbridge HeathBroadbridge Heath 0-2 Sittingbourne | Isthmian League - South East Division |
| 25 | Tue 23 Jan | 161-2 v Hythe TownHythe Town 2-1 Sittingbourne | Kent Senior Cup Second Round |
| 26 | Sat 27 Jan | 83-0 v Herne BayHerne Bay 0-3 Sittingbourne | Isthmian League - South East Division |
| 27 | Tue 30 Jan | 82-1 v East Grinstead TownEast Grinstead Town 1-2 Sittingbourne | Isthmian League - South East Division |
| 28 | Sat 3 Feb | 125-0 v Burgess Hill TownSittingbourne 5-0 Burgess Hill Town | Isthmian League - South East Division |
| 29 | Tue 6 Feb | 122-1 v Sevenoaks TownSittingbourne 2-1 Sevenoaks Town | Isthmian League - South East Division |
| 30 | Sun 11 Feb | 64-0 v Erith & BelvedereErith & Belvedere 0-4 Sittingbourne | Isthmian League - South East Division |
| 31 | Sat 17 Feb | 60-3 v Chichester CitySittingbourne 0-3 Chichester City | Isthmian League - South East Division |
| 32 | Sat 2 Mar | 62-0 v East Grinstead TownSittingbourne 2-0 East Grinstead Town | Isthmian League - South East Division |
| 33 | Sat 9 Mar | 65-1 v Ashford UnitedAshford United 1-5 Sittingbourne | Isthmian League - South East Division |
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