| 1 | Sat 6 Jul | 84-1 v Faversham TownFaversham Town 1-4 Sittingbourne | Friendly |
| 2 | Sat 3 Aug | 85-1 v BromleySittingbourne 5-1 Bromley | Friendly |
| 3 | Sat 10 Aug | 145-0 v Broadbridge HeathSittingbourne 5-0 Broadbridge Heath | Isthmian League - South East Division |
| 4 | Sat 17 Aug | 144-2 v Farnham TownFarnham Town 2-4 Sittingbourne | Emirates FA Cup Preliminary Round |
| 5 | Sat 24 Aug | 142-4 v RamsgateRamsgate 4-2 Sittingbourne | Isthmian League - South East Division |
| 6 | Mon 26 Aug | 103-1 v Ashford UnitedSittingbourne 3-1 Ashford United | Isthmian League - South East Division |
| 7 | Sat 31 Aug | 102-2 v Dover AthleticSittingbourne 2-2 Dover Athletic | Emirates FA Cup First Qualifying Round |
| 8 | Tue 3 Sep | 21-0 v Dover AthleticDover Athletic 0-1 Sittingbourne | Emirates FA Cup First Qualifying Round Replay |
| 9 | Sat 7 Sep | 2 2-0 v Sutton Common RoversSittingbourne 2-0 Sutton Common Rovers | Isuzu FA Trophy First Qualifying Round |
| 10 | Tue 10 Sep | 24-0 v Phoenix SportsSittingbourne 4-0 Phoenix Sports | Isthmian League - South East Division |
| 11 | Sat 14 Sep | 21-0 v Lordswood AFCLordswood AFC 0-1 Sittingbourne | Emirates FA Cup Second Qualifying Round |
| 12 | Tue 17 Sep | 81-4 v Erith TownErith Town 4-1 Sittingbourne | Velocity Cup Second Round |
| 13 | Sat 21 Sep | 24-1 v KingstonianSittingbourne 4-1 Kingstonian | Isuzu FA Trophy Second Qualifying Round |
| 14 | Sat 28 Sep | 20-3 v Plymouth ParkwaySittingbourne 0-3 Plymouth Parkway | Emirates FA Cup Third Qualifying Round |
| 15 | Tue 1 Oct | 22-0 v Burgess Hill TownBurgess Hill Town 0-2 Sittingbourne | Isthmian League - South East Division |
| 16 | Sat 5 Oct | 102-1 v Bognor Regis TownSittingbourne 2-1 Bognor Regis Town | Isuzu FA Trophy Third Qualifying Round |
| 17 | Tue 8 Oct | 103-2 v Deal TownDeal Town 2-3 Sittingbourne | Isthmian League - South East Division |
| 18 | Sat 12 Oct | 172-2 v Beckenham TownBeckenham Town 2-2 Sittingbourne | Isthmian League - South East Division |
| 19 | Sat 19 Oct | 86-0 v Hythe TownSittingbourne 6-0 Hythe Town | Isthmian League - South East Division |
| 20 | Tue 22 Oct | 144-1 v Herne BaySittingbourne 4-1 Herne Bay | Isthmian League - South East Division |
| 21 | Sat 26 Oct | 8 2-0 v Dover AthleticDover Athletic 0-2 Sittingbourne | Isuzu FA Trophy First Round |
| 22 | Tue 29 Oct | 45-0 v Steyning Town CommunitySittingbourne 5-0 Steyning Town Community | Isthmian League - South East Division |
| 23 | Sat 2 Nov | 103-0 v Three BridgesSittingbourne 3-0 Three Bridges | Isthmian League - South East Division |
| 24 | Tue 5 Nov | 143-0 v Phoenix SportsPhoenix Sports 0-3 Sittingbourne | Isthmian League - South East Division |
| 25 | Sat 9 Nov | 105-0 v Deal TownSittingbourne 5-0 Deal Town | Isthmian League - South East Division |
| 26 | Sat 16 Nov | 81-1 v Winchester CityWinchester City 1-1 Sittingbourne | Isuzu FA Trophy Second Round |
| 27 | Sat 23 Nov | 83-0 v Sevenoaks TownSittingbourne 3-0 Sevenoaks Town | Isthmian League - South East Division |
| 28 | Sat 30 Nov | 83-1 v AFC Croydon AthleticSittingbourne 3-1 AFC Croydon Athletic | Isthmian League - South East Division |
| 29 | Tue 3 Dec | 81-0 v Littlehampton TownLittlehampton Town 0-1 Sittingbourne | Isthmian League - South East Division |
| 30 | Sat 7 Dec | 124-2 v Enfield TownSittingbourne 4-2 Enfield Town | Isuzu FA Trophy Third Round |
| 31 | Tue 10 Dec | 84-0 v Herne BayHerne Bay 0-4 Sittingbourne | Isthmian League - South East Division |
| 32 | Sat 14 Dec | 122-0 v MersthamSittingbourne 2-0 Merstham | Isthmian League - South East Division |
| 33 | Thu 26 Dec | 124-0 v Sheppey UnitedSittingbourne 4-0 Sheppey United | Isthmian League - South East Division |
| 34 | Sat 28 Dec | 23-2 v Broadbridge HeathBroadbridge Heath 2-3 Sittingbourne | Isthmian League - South East Division |
| 35 | Wed 1 Jan | 141-1 v Ashford UnitedAshford United 1-1 Sittingbourne | Isthmian League - South East Division |
| 36 | Sat 18 Jan | 148-1 v LancingSittingbourne 8-1 Lancing | Isthmian League - South East Division |
| 37 | Tue 21 Jan | 83-0 v East Grinstead TownSittingbourne 3-0 East Grinstead Town | Isthmian League - South East Division |
| 38 | Sat 25 Jan | 84-0 v AFC Croydon AthleticAFC Croydon Athletic 0-4 Sittingbourne | Isthmian League - South East Division |
| 39 | Sat 1 Feb | 111-0 v Southend UnitedSouthend United 0-1 Sittingbourne | Isuzu FA Trophy Fifth Round |
| 40 | Tue 4 Feb | 151-1 v Erith TownErith Town 1-1 Sittingbourne | Isthmian League - South East Division |
| 41 | Sat 8 Feb | 82-1 v Steyning Town CommunitySteyning Town Community 1-2 Sittingbourne | Isthmian League - South East Division |
| 42 | Sat 15 Feb | 140-0 v Beckenham TownSittingbourne 0-0 Beckenham Town | Isthmian League - South East Division |
| 43 | Tue 18 Feb | 173-0 v MargateSittingbourne 3-0 Margate | Isthmian League - South East Division |
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