| 1 | Sat 9 Aug | 13-1 v Deal TownDeal Town 1-3 Sittingbourne | Isthmian League - South East Division |
| 2 | Tue 12 Aug | 12-1 v MargateSittingbourne 2-1 Margate | Isthmian League - South East Division |
| 3 | Sat 16 Aug | 11-0 v VCD AthleticVCD Athletic 0-1 Sittingbourne | Emirates FA Cup Preliminary Round |
| 4 | Sat 23 Aug | 12-1 v East Grinstead TownSittingbourne 2-1 East Grinstead Town | Isthmian League - South East Division |
| 5 | Mon 25 Aug | 11-2 v Sheppey UnitedSheppey United 2-1 Sittingbourne | Isthmian League - South East Division |
| 6 | Sat 30 Aug | 11-2 v AFC Croydon AthleticSittingbourne 1-2 AFC Croydon Athletic | Emirates FA Cup First Qualifying Round |
| 7 | Tue 2 Sep | 12-2 v Beckenham TownBeckenham Town 2-2 Sittingbourne | Isthmian League - South East Division |
| 8 | Tue 16 Sep | 11-1 v Hastings UnitedSittingbourne 1-1 Hastings United | Isthmian League - South East Division |
| 9 | Sat 27 Sep | 11-1 v Erith TownSittingbourne 1-1 Erith Town | Isthmian League - South East Division |
| 10 | Tue 30 Sep | 11-1 v Jersey BullsJersey Bulls 1-1 Sittingbourne | Isthmian League - South East Division |
| 11 | Sat 4 Oct | 11-0 v Hashtag UnitedSittingbourne 1-0 Hashtag United | Isuzu FA Trophy Third Qualifying Round |
| 12 | Sat 18 Oct | 11-3 v Faversham TownSittingbourne 1-3 Faversham Town | Isthmian League - South East Division |
| 13 | Sat 25 Oct | 12-1 v Cray Valley PMSittingbourne 2-1 Cray Valley PM | Isuzu FA Trophy First Round |
| 14 | Tue 28 Oct | 10-4 v Crowborough AthleticCrowborough Athletic 4-0 Sittingbourne | Velocity Cup Second Round |
| 15 | Sat 1 Nov | 14-3 v AFC Croydon AthleticSittingbourne 4-3 AFC Croydon Athletic | Isthmian League - South East Division |
| 16 | Wed 5 Nov | 10-1 v Sevenoaks TownSevenoaks Town 1-0 Sittingbourne | Isthmian League - South East Division |
| 17 | Sat 8 Nov | 11-2 v Three BridgesThree Bridges 2-1 Sittingbourne | Isthmian League - South East Division |
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