| 1 | Sat 6 Jul | 64-1 v Faversham TownFaversham Town 1-4 Sittingbourne | Friendly |
| 2 | Thu 25 Jul | 52-2 v Bowers & PitseaSittingbourne 2-2 Bowers & Pitsea | Friendly |
| 3 | Sat 3 Aug | 35-1 v BromleySittingbourne 5-1 Bromley | Friendly |
| 4 | Sat 10 Aug | 55-0 v Broadbridge HeathSittingbourne 5-0 Broadbridge Heath | Isthmian League - South East Division |
| 5 | Sat 17 Aug | 54-2 v Farnham TownFarnham Town 2-4 Sittingbourne | Emirates FA Cup Preliminary Round |
| 6 | Sat 24 Aug | 52-4 v RamsgateRamsgate 4-2 Sittingbourne | Isthmian League - South East Division |
| 7 | Mon 26 Aug | 53-1 v Ashford UnitedSittingbourne 3-1 Ashford United | Isthmian League - South East Division |
| 8 | Sat 31 Aug | 52-2 v Dover AthleticSittingbourne 2-2 Dover Athletic | Emirates FA Cup First Qualifying Round |
| 9 | Tue 3 Sep | 51-0 v Dover AthleticDover Athletic 0-1 Sittingbourne | Emirates FA Cup First Qualifying Round Replay |
| 10 | Sat 7 Sep | 52-0 v Sutton Common RoversSittingbourne 2-0 Sutton Common Rovers | Isuzu FA Trophy First Qualifying Round |
| 11 | Tue 10 Sep | 5 4-0 v Phoenix SportsSittingbourne 4-0 Phoenix Sports | Isthmian League - South East Division |
| 12 | Sat 14 Sep | 51-0 v Lordswood AFCLordswood AFC 0-1 Sittingbourne | Emirates FA Cup Second Qualifying Round |
| 13 | Sat 21 Sep | 54-1 v KingstonianSittingbourne 4-1 Kingstonian | Isuzu FA Trophy Second Qualifying Round |
| 14 | Sat 28 Sep | 50-3 v Plymouth ParkwaySittingbourne 0-3 Plymouth Parkway | Emirates FA Cup Third Qualifying Round |
| 15 | Sat 5 Oct | 2 2-1 v Bognor Regis TownSittingbourne 2-1 Bognor Regis Town | Isuzu FA Trophy Third Qualifying Round |
| 16 | Tue 8 Oct | 23-2 v Deal TownDeal Town 2-3 Sittingbourne | Isthmian League - South East Division |
| 17 | Sat 12 Oct | 22-2 v Beckenham TownBeckenham Town 2-2 Sittingbourne | Isthmian League - South East Division |
| 18 | Wed 16 Oct | 51-1 v Sevenoaks TownSevenoaks Town 1-1 Sittingbourne | Isthmian League - South East Division |
| 19 | Sat 19 Oct | 56-0 v Hythe TownSittingbourne 6-0 Hythe Town | Isthmian League - South East Division |
| 20 | Tue 22 Oct | 54-1 v Herne BaySittingbourne 4-1 Herne Bay | Isthmian League - South East Division |
| 21 | Sat 26 Oct | 52-0 v Dover AthleticDover Athletic 0-2 Sittingbourne | Isuzu FA Trophy First Round |
| 22 | Tue 29 Oct | 55-0 v Steyning Town CommunitySittingbourne 5-0 Steyning Town Community | Isthmian League - South East Division |
| 23 | Sat 2 Nov | 53-0 v Three BridgesSittingbourne 3-0 Three Bridges | Isthmian League - South East Division |
| 24 | Tue 5 Nov | 53-0 v Phoenix SportsPhoenix Sports 0-3 Sittingbourne | Isthmian League - South East Division |
| 25 | Sat 16 Nov | 41-1 v Winchester CityWinchester City 1-1 Sittingbourne | Isuzu FA Trophy Second Round |
| 26 | Sat 23 Nov | 53-0 v Sevenoaks TownSittingbourne 3-0 Sevenoaks Town | Isthmian League - South East Division |
| 27 | Sat 30 Nov | 53-1 v AFC Croydon AthleticSittingbourne 3-1 AFC Croydon Athletic | Isthmian League - South East Division |
| 28 | Tue 3 Dec | 51-0 v Littlehampton TownLittlehampton Town 0-1 Sittingbourne | Isthmian League - South East Division |
| 29 | Sat 7 Dec | 84-2 v Enfield TownSittingbourne 4-2 Enfield Town | Isuzu FA Trophy Third Round |
| 30 | Tue 10 Dec | 24-0 v Herne BayHerne Bay 0-4 Sittingbourne | Isthmian League - South East Division |
| 31 | Sat 14 Dec | 22-0 v MersthamSittingbourne 2-0 Merstham | Isthmian League - South East Division |
| 32 | Sat 21 Dec | 22-1 v Eastbourne TownEastbourne Town 1-2 Sittingbourne | Isthmian League - South East Division |
| 33 | Thu 26 Dec | 24-0 v Sheppey UnitedSittingbourne 4-0 Sheppey United | Isthmian League - South East Division |
| 34 | Sat 28 Dec | 33-2 v Broadbridge HeathBroadbridge Heath 2-3 Sittingbourne | Isthmian League - South East Division |
| 35 | Wed 1 Jan | 21-1 v Ashford UnitedAshford United 1-1 Sittingbourne | Isthmian League - South East Division |
| 36 | Sat 4 Jan | 2 2-1 v SalisburySittingbourne 2-1 Salisbury | Isuzu FA Trophy Fourth Round |
| 37 | Sat 18 Jan | 28-1 v LancingSittingbourne 8-1 Lancing | Isthmian League - South East Division |
| 38 | Tue 21 Jan | 23-0 v East Grinstead TownSittingbourne 3-0 East Grinstead Town | Isthmian League - South East Division |
| 39 | Sat 25 Jan | 64-0 v AFC Croydon AthleticAFC Croydon Athletic 0-4 Sittingbourne | Isthmian League - South East Division |
| 40 | Sat 1 Feb | 41-0 v Southend UnitedSouthend United 0-1 Sittingbourne | Isuzu FA Trophy Fifth Round |
| 41 | Tue 4 Feb | 6 1-1 v Erith TownErith Town 1-1 Sittingbourne | Isthmian League - South East Division |
| 42 | Sat 8 Feb | 52-1 v Steyning Town CommunitySteyning Town Community 1-2 Sittingbourne | Isthmian League - South East Division |
| 43 | Sat 15 Feb | 50-0 v Beckenham TownSittingbourne 0-0 Beckenham Town | Isthmian League - South East Division |
| 44 | Tue 18 Feb | 53-0 v MargateSittingbourne 3-0 Margate | Isthmian League - South East Division |
| 45 | Sat 1 Mar | 5 0-3 v Aldershot TownSittingbourne 0-3 Aldershot Town | Isuzu FA Trophy Quarter Final |
| 46 | Tue 4 Mar | 53-0 v MargateMargate 0-3 Sittingbourne | Isthmian League - South East Division |
| 47 | Sat 8 Mar | 52-3 v Three BridgesThree Bridges 3-2 Sittingbourne | Isthmian League - South East Division |
| 48 | Tue 11 Mar | 53-1 v Littlehampton TownSittingbourne 3-1 Littlehampton Town | Isthmian League - South East Division |
| 49 | Sat 15 Mar | 50-1 v MersthamMerstham 1-0 Sittingbourne | Isthmian League - South East Division |
| 50 | Tue 18 Mar | 5 2-1 v Hythe TownHythe Town 1-2 Sittingbourne | Isthmian League - South East Division |
| 51 | Sat 22 Mar | 2 2-0 v Eastbourne TownSittingbourne 2-0 Eastbourne Town | Isthmian League - South East Division |
| 52 | Sat 29 Mar | 51-0 v LancingLancing 0-1 Sittingbourne | Isthmian League - South East Division |
| 53 | Sat 5 Apr | 53-0 v Erith TownSittingbourne 3-0 Erith Town | Isthmian League - South East Division |
| 54 | Sat 12 Apr | 5 5-0 v East Grinstead TownEast Grinstead Town 0-5 Sittingbourne | Isthmian League - South East Division |
| 55 | Fri 18 Apr | 51-1 v Burgess Hill TownSittingbourne 1-1 Burgess Hill Town | Isthmian League - South East Division |
| 56 | Mon 21 Apr | 50-0 v Sheppey UnitedSheppey United 0-0 Sittingbourne | Isthmian League - South East Division |
| 57 | Sat 26 Apr | 53-3 v RamsgateSittingbourne 3-3 Ramsgate | Isthmian League - South East Division |
| 58 | Tue 29 Apr | 54-2 v MersthamSittingbourne 4-2 Merstham | Isthmian League - South East Division Play-off Semi Final |
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