| 1 | Sat 6 Jul | 14-1 v Faversham TownFaversham Town 1-4 Sittingbourne | Friendly |
| 2 | Thu 25 Jul | 12-2 v Bowers & PitseaSittingbourne 2-2 Bowers & Pitsea | Friendly |
| 3 | Sat 3 Aug | 15-1 v BromleySittingbourne 5-1 Bromley | Friendly |
| 4 | Sat 10 Aug | 15-0 v Broadbridge HeathSittingbourne 5-0 Broadbridge Heath | Isthmian League - South East Division |
| 5 | Sat 17 Aug | 14-2 v Farnham TownFarnham Town 2-4 Sittingbourne | Emirates FA Cup Preliminary Round |
| 6 | Sat 24 Aug | 12-4 v RamsgateRamsgate 4-2 Sittingbourne | Isthmian League - South East Division |
| 7 | Mon 26 Aug | 13-1 v Ashford UnitedSittingbourne 3-1 Ashford United | Isthmian League - South East Division |
| 8 | Sat 31 Aug | 12-2 v Dover AthleticSittingbourne 2-2 Dover Athletic | Emirates FA Cup First Qualifying Round |
| 9 | Tue 3 Sep | 11-0 v Dover AthleticDover Athletic 0-1 Sittingbourne | Emirates FA Cup First Qualifying Round Replay |
| 10 | Sat 7 Sep | 12-0 v Sutton Common RoversSittingbourne 2-0 Sutton Common Rovers | Isuzu FA Trophy First Qualifying Round |
| 11 | Tue 17 Sep | 11-4 v Erith TownErith Town 4-1 Sittingbourne | Velocity Cup Second Round |
| 12 | Tue 24 Sep | 11-6 v Deal TownDeal Town 6-1 Sittingbourne | Kent Senior Cup First Round |
| 13 | Wed 16 Oct | 11-1 v Sevenoaks TownSevenoaks Town 1-1 Sittingbourne | Isthmian League - South East Division |
| 14 | Sat 19 Oct | 16-0 v Hythe TownSittingbourne 6-0 Hythe Town | Isthmian League - South East Division |
| 15 | Tue 22 Oct | 14-1 v Herne BaySittingbourne 4-1 Herne Bay | Isthmian League - South East Division |
| 16 | Sat 26 Oct | 12-0 v Dover AthleticDover Athletic 0-2 Sittingbourne | Isuzu FA Trophy First Round |
| 17 | Tue 29 Oct | 15-0 v Steyning Town CommunitySittingbourne 5-0 Steyning Town Community | Isthmian League - South East Division |
| 18 | Sat 2 Nov | 1 3-0 v Three BridgesSittingbourne 3-0 Three Bridges | Isthmian League - South East Division |
| 19 | Tue 5 Nov | 13-0 v Phoenix SportsPhoenix Sports 0-3 Sittingbourne | Isthmian League - South East Division |
| 20 | Sat 9 Nov | 15-0 v Deal TownSittingbourne 5-0 Deal Town | Isthmian League - South East Division |
| 21 | Sat 16 Nov | 11-1 v Winchester CityWinchester City 1-1 Sittingbourne | Isuzu FA Trophy Second Round |
| 22 | Sat 23 Nov | 13-0 v Sevenoaks TownSittingbourne 3-0 Sevenoaks Town | Isthmian League - South East Division |
| 23 | Sat 30 Nov | 13-1 v AFC Croydon AthleticSittingbourne 3-1 AFC Croydon Athletic | Isthmian League - South East Division |
| 24 | Tue 3 Dec | 11-0 v Littlehampton TownLittlehampton Town 0-1 Sittingbourne | Isthmian League - South East Division |
| 25 | Sat 7 Dec | 14-2 v Enfield TownSittingbourne 4-2 Enfield Town | Isuzu FA Trophy Third Round |
| 26 | Tue 10 Dec | 14-0 v Herne BayHerne Bay 0-4 Sittingbourne | Isthmian League - South East Division |
| 27 | Sat 14 Dec | 12-0 v MersthamSittingbourne 2-0 Merstham | Isthmian League - South East Division |
| 28 | Sat 21 Dec | 12-1 v Eastbourne TownEastbourne Town 1-2 Sittingbourne | Isthmian League - South East Division |
| 29 | Thu 26 Dec | 14-0 v Sheppey UnitedSittingbourne 4-0 Sheppey United | Isthmian League - South East Division |
| 30 | Sat 28 Dec | 13-2 v Broadbridge HeathBroadbridge Heath 2-3 Sittingbourne | Isthmian League - South East Division |
| 31 | Wed 1 Jan | 11-1 v Ashford UnitedAshford United 1-1 Sittingbourne | Isthmian League - South East Division |
| 32 | Sat 4 Jan | 12-1 v SalisburySittingbourne 2-1 Salisbury | Isuzu FA Trophy Fourth Round |
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