| 1 | Thu 25 Jul | 22-2 v Bowers & PitseaSittingbourne 2-2 Bowers & Pitsea | Friendly |
| 2 | Sat 10 Aug | 165-0 v Broadbridge HeathSittingbourne 5-0 Broadbridge Heath | Isthmian League - South East Division |
| 3 | Sat 17 Aug | 154-2 v Farnham TownFarnham Town 2-4 Sittingbourne | Emirates FA Cup Preliminary Round |
| 4 | Sat 24 Aug | 112-4 v RamsgateRamsgate 4-2 Sittingbourne | Isthmian League - South East Division |
| 5 | Mon 26 Aug | 143-1 v Ashford UnitedSittingbourne 3-1 Ashford United | Isthmian League - South East Division |
| 6 | Sat 31 Aug | 142-2 v Dover AthleticSittingbourne 2-2 Dover Athletic | Emirates FA Cup First Qualifying Round |
| 7 | Tue 3 Sep | 141-0 v Dover AthleticDover Athletic 0-1 Sittingbourne | Emirates FA Cup First Qualifying Round Replay |
| 8 | Sat 7 Sep | 42-0 v Sutton Common RoversSittingbourne 2-0 Sutton Common Rovers | Isuzu FA Trophy First Qualifying Round |
| 9 | Tue 10 Sep | 114-0 v Phoenix SportsSittingbourne 4-0 Phoenix Sports | Isthmian League - South East Division |
| 10 | Sat 14 Sep | 151-0 v Lordswood AFCLordswood AFC 0-1 Sittingbourne | Emirates FA Cup Second Qualifying Round |
| 11 | Tue 17 Sep | 111-4 v Erith TownErith Town 4-1 Sittingbourne | Velocity Cup Second Round |
| 12 | Sat 21 Sep | 144-1 v KingstonianSittingbourne 4-1 Kingstonian | Isuzu FA Trophy Second Qualifying Round |
| 13 | Tue 24 Sep | 111-6 v Deal TownDeal Town 6-1 Sittingbourne | Kent Senior Cup First Round |
| 14 | Sat 28 Sep | 140-3 v Plymouth ParkwaySittingbourne 0-3 Plymouth Parkway | Emirates FA Cup Third Qualifying Round |
| 15 | Tue 1 Oct | 72-0 v Burgess Hill TownBurgess Hill Town 0-2 Sittingbourne | Isthmian League - South East Division |
| 16 | Sat 5 Oct | 142-1 v Bognor Regis TownSittingbourne 2-1 Bognor Regis Town | Isuzu FA Trophy Third Qualifying Round |
| 17 | Tue 8 Oct | 143-2 v Deal TownDeal Town 2-3 Sittingbourne | Isthmian League - South East Division |
| 18 | Sat 12 Oct | 122-2 v Beckenham TownBeckenham Town 2-2 Sittingbourne | Isthmian League - South East Division |
| 19 | Wed 16 Oct | 101-1 v Sevenoaks TownSevenoaks Town 1-1 Sittingbourne | Isthmian League - South East Division |
| 20 | Sat 19 Oct | 106-0 v Hythe TownSittingbourne 6-0 Hythe Town | Isthmian League - South East Division |
| 21 | Tue 22 Oct | 154-1 v Herne BaySittingbourne 4-1 Herne Bay | Isthmian League - South East Division |
| 22 | Sat 26 Oct | 11 2-0 v Dover AthleticDover Athletic 0-2 Sittingbourne | Isuzu FA Trophy First Round |
| 23 | Tue 29 Oct | 175-0 v Steyning Town CommunitySittingbourne 5-0 Steyning Town Community | Isthmian League - South East Division |
| 24 | Sat 2 Nov | 163-0 v Three BridgesSittingbourne 3-0 Three Bridges | Isthmian League - South East Division |
| 25 | Tue 5 Nov | 113-0 v Phoenix SportsPhoenix Sports 0-3 Sittingbourne | Isthmian League - South East Division |
| 26 | Tue 10 Dec | 174-0 v Herne BayHerne Bay 0-4 Sittingbourne | Isthmian League - South East Division |
| 27 | Sat 14 Dec | 142-0 v MersthamSittingbourne 2-0 Merstham | Isthmian League - South East Division |
| 28 | Thu 26 Dec | 144-0 v Sheppey UnitedSittingbourne 4-0 Sheppey United | Isthmian League - South East Division |
| 29 | Sat 28 Dec | 123-2 v Broadbridge HeathBroadbridge Heath 2-3 Sittingbourne | Isthmian League - South East Division |
| 30 | Wed 1 Jan | 81-1 v Ashford UnitedAshford United 1-1 Sittingbourne | Isthmian League - South East Division |
| 31 | Sat 18 Jan | 158-1 v LancingSittingbourne 8-1 Lancing | Isthmian League - South East Division |
| 32 | Tue 21 Jan | 153-0 v East Grinstead TownSittingbourne 3-0 East Grinstead Town | Isthmian League - South East Division |
| 33 | Sat 25 Jan | 144-0 v AFC Croydon AthleticAFC Croydon Athletic 0-4 Sittingbourne | Isthmian League - South East Division |
| 34 | Sat 1 Feb | 161-0 v Southend UnitedSouthend United 0-1 Sittingbourne | Isuzu FA Trophy Fifth Round |
| 35 | Tue 4 Feb | 141-1 v Erith TownErith Town 1-1 Sittingbourne | Isthmian League - South East Division |
| 36 | Sat 8 Feb | 112-1 v Steyning Town CommunitySteyning Town Community 1-2 Sittingbourne | Isthmian League - South East Division |
| 37 | Sat 15 Feb | 150-0 v Beckenham TownSittingbourne 0-0 Beckenham Town | Isthmian League - South East Division |
| 38 | Tue 18 Feb | 153-0 v MargateSittingbourne 3-0 Margate | Isthmian League - South East Division |
| 39 | Sat 1 Mar | 120-3 v Aldershot TownSittingbourne 0-3 Aldershot Town | Isuzu FA Trophy Quarter Final |
| 40 | Tue 4 Mar | 153-0 v MargateMargate 0-3 Sittingbourne | Isthmian League - South East Division |
| 41 | Sat 8 Mar | 112-3 v Three BridgesThree Bridges 3-2 Sittingbourne | Isthmian League - South East Division |
| 42 | Tue 11 Mar | 123-1 v Littlehampton TownSittingbourne 3-1 Littlehampton Town | Isthmian League - South East Division |
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