| 1 | Sat 30 Aug | 144-0 v MarlowChatham Town 4-0 Marlow | Emirates FA Cup First Qualifying Round |
| 2 | Sat 6 Sep | 583-0 v Wingate & FinchleyWingate & Finchley 0-3 Chatham Town | Isthmian League - Premier Division |
| 3 | Tue 9 Sep | 14 4-1 v Beckenham TownChatham Town 4-1 Beckenham Town | Kent Senior Cup |
| 4 | Sat 13 Sep | 143-0 v Ashford UnitedAshford United 0-3 Chatham Town | Emirates FA Cup Second Qualifying Round |
| 5 | Tue 16 Sep | 583-1 v Cray Valley PMChatham Town 3-1 Cray Valley PM | Isthmian League - Premier Division |
| 6 | Sat 20 Sep | 58 2-1 v Carshalton AthleticChatham Town 2-1 Carshalton Athletic | Isthmian League - Premier Division |
| 7 | Sat 27 Sep | 143-1 v Deal TownChatham Town 3-1 Deal Town | Emirates FA Cup Third Qualifying Round |
| 8 | Sat 4 Oct | 140-0 v Needham MarketChatham Town 0-0 Needham Market | Isuzu FA Trophy Third Qualifying Round |
| 9 | Sat 11 Oct | 143-1 v Tonbridge AngelsTonbridge Angels 1-3 Chatham Town | Emirates FA Cup Fourth Qualifying Round |
| 10 | Tue 14 Oct | 58 1-0 v Cray Valley PMCray Valley PM 0-1 Chatham Town | Isthmian League - Premier Division |
| 11 | Sat 18 Oct | 583-3 v Cray WanderersChatham Town 3-3 Cray Wanderers | Isthmian League - Premier Division |
| 12 | Tue 21 Oct | 580-0 v Dulwich HamletChatham Town 0-0 Dulwich Hamlet | Isthmian League - Premier Division |
| 13 | Sat 25 Oct | 142-0 v Waltham AbbeyWaltham Abbey 0-2 Chatham Town | Isuzu FA Trophy First Round |
| 14 | Tue 28 Oct | 14 3-1 v Erith TownErith Town 1-3 Chatham Town | Kent Senior Cup |
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