| 1 | Sat 3 Aug | 25-1 v BromleySittingbourne 5-1 Bromley | Friendly |
| 2 | Sat 10 Aug | 25-0 v Broadbridge HeathSittingbourne 5-0 Broadbridge Heath | Isthmian League - South East Division |
| 3 | Sat 17 Aug | 34-2 v Farnham TownFarnham Town 2-4 Sittingbourne | Emirates FA Cup Preliminary Round |
| 4 | Sat 24 Aug | 3 2-4 v RamsgateRamsgate 4-2 Sittingbourne | Isthmian League - South East Division |
| 5 | Mon 26 Aug | 23-1 v Ashford UnitedSittingbourne 3-1 Ashford United | Isthmian League - South East Division |
| 6 | Sat 31 Aug | 22-2 v Dover AthleticSittingbourne 2-2 Dover Athletic | Emirates FA Cup First Qualifying Round |
| 7 | Sat 5 Oct | 182-1 v Bognor Regis TownSittingbourne 2-1 Bognor Regis Town | Isuzu FA Trophy Third Qualifying Round |
| 8 | Sat 12 Oct | 162-2 v Beckenham TownBeckenham Town 2-2 Sittingbourne | Isthmian League - South East Division |
| 9 | Wed 16 Oct | 3 1-1 v Sevenoaks TownSevenoaks Town 1-1 Sittingbourne | Isthmian League - South East Division |
| 10 | Sat 19 Oct | 26-0 v Hythe TownSittingbourne 6-0 Hythe Town | Isthmian League - South East Division |
| 11 | Tue 22 Oct | 24-1 v Herne BaySittingbourne 4-1 Herne Bay | Isthmian League - South East Division |
| 12 | Sat 26 Oct | 22-0 v Dover AthleticDover Athletic 0-2 Sittingbourne | Isuzu FA Trophy First Round |
| 13 | Tue 29 Oct | 25-0 v Steyning Town CommunitySittingbourne 5-0 Steyning Town Community | Isthmian League - South East Division |
| 14 | Sat 2 Nov | 23-0 v Three BridgesSittingbourne 3-0 Three Bridges | Isthmian League - South East Division |
| 15 | Tue 5 Nov | 23-0 v Phoenix SportsPhoenix Sports 0-3 Sittingbourne | Isthmian League - South East Division |
| 16 | Sat 9 Nov | 25-0 v Deal TownSittingbourne 5-0 Deal Town | Isthmian League - South East Division |
| 17 | Sat 16 Nov | 21-1 v Winchester CityWinchester City 1-1 Sittingbourne | Isuzu FA Trophy Second Round |
| 18 | Sat 23 Nov | 2 3-0 v Sevenoaks TownSittingbourne 3-0 Sevenoaks Town | Isthmian League - South East Division |
| 19 | Sat 30 Nov | 23-1 v AFC Croydon AthleticSittingbourne 3-1 AFC Croydon Athletic | Isthmian League - South East Division |
| 20 | Wed 1 Jan | 151-1 v Ashford UnitedAshford United 1-1 Sittingbourne | Isthmian League - South East Division |
| 21 | Sat 25 Jan | 124-0 v AFC Croydon AthleticAFC Croydon Athletic 0-4 Sittingbourne | Isthmian League - South East Division |
| 22 | Sat 1 Feb | 21-0 v Southend UnitedSouthend United 0-1 Sittingbourne | Isuzu FA Trophy Fifth Round |
| 23 | Tue 4 Feb | 21-1 v Erith TownErith Town 1-1 Sittingbourne | Isthmian League - South East Division |
| 24 | Sat 8 Feb | 22-1 v Steyning Town CommunitySteyning Town Community 1-2 Sittingbourne | Isthmian League - South East Division |
| 25 | Sat 15 Feb | 120-0 v Beckenham TownSittingbourne 0-0 Beckenham Town | Isthmian League - South East Division |
| 26 | Tue 18 Feb | 23-0 v MargateSittingbourne 3-0 Margate | Isthmian League - South East Division |
| 27 | Sat 1 Mar | 20-3 v Aldershot TownSittingbourne 0-3 Aldershot Town | Isuzu FA Trophy Quarter Final |
| 28 | Tue 4 Mar | 2 3-0 v MargateMargate 0-3 Sittingbourne | Isthmian League - South East Division |
| 29 | Sat 8 Mar | 22-3 v Three BridgesThree Bridges 3-2 Sittingbourne | Isthmian League - South East Division |
| 30 | Tue 11 Mar | 23-1 v Littlehampton TownSittingbourne 3-1 Littlehampton Town | Isthmian League - South East Division |
| 31 | Sat 15 Mar | 2 0-1 v MersthamMerstham 1-0 Sittingbourne | Isthmian League - South East Division |
| 32 | Tue 18 Mar | 22-1 v Hythe TownHythe Town 1-2 Sittingbourne | Isthmian League - South East Division |
| 33 | Sat 22 Mar | 142-0 v Eastbourne TownSittingbourne 2-0 Eastbourne Town | Isthmian League - South East Division |
| 34 | Sat 29 Mar | 21-0 v LancingLancing 0-1 Sittingbourne | Isthmian League - South East Division |
| 35 | Sat 5 Apr | 23-0 v Erith TownSittingbourne 3-0 Erith Town | Isthmian League - South East Division |
| 36 | Sat 12 Apr | 25-0 v East Grinstead TownEast Grinstead Town 0-5 Sittingbourne | Isthmian League - South East Division |
| 37 | Fri 18 Apr | 21-1 v Burgess Hill TownSittingbourne 1-1 Burgess Hill Town | Isthmian League - South East Division |
| 38 | Sat 26 Apr | 23-3 v RamsgateSittingbourne 3-3 Ramsgate | Isthmian League - South East Division |
| 39 | Tue 29 Apr | 24-2 v MersthamSittingbourne 4-2 Merstham | Isthmian League - South East Division Play-off Semi Final |
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