| 1 | Sat 3 Aug | 33-2 v Herne BayHerne Bay 2-3 Chatham Town | Friendly |
| 2 | Sat 10 Aug | 30-2 v LewesLewes 2-0 Chatham Town | Isthmian League - Premier Division |
| 3 | Tue 13 Aug | 3 1-1 v Billericay TownChatham Town 1-1 Billericay Town | Isthmian League - Premier Division |
| 4 | Sat 17 Aug | 32-0 v Bowers & PitseaBowers & Pitsea 0-2 Chatham Town | Isthmian League - Premier Division |
| 5 | Sat 24 Aug | 33-1 v Dulwich HamletChatham Town 3-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 6 | Mon 26 Aug | 3 1-3 v DartfordDartford 3-1 Chatham Town | Isthmian League - Premier Division |
| 7 | Sat 31 Aug | 32-0 v WestfieldWestfield 0-2 Chatham Town | Emirates FA Cup First Qualifying Round |
| 8 | Sat 7 Sep | 32-2 v HendonChatham Town 2-2 Hendon | Isthmian League - Premier Division |
| 9 | Sat 14 Sep | 3 1-0 v Welling UnitedWelling United 0-1 Chatham Town | Emirates FA Cup Second Qualifying Round |
| 10 | Sat 21 Sep | 31-3 v Canvey IslandChatham Town 1-3 Canvey Island | Isthmian League - Premier Division |
| 11 | Tue 24 Sep | 31-2 v Cray WanderersChatham Town 1-2 Cray Wanderers | Kent Senior Cup First Round |
| 12 | Sat 28 Sep | 3 0-3 v Slough TownChatham Town 0-3 Slough Town | Emirates FA Cup Third Qualifying Round |
| 13 | Tue 1 Oct | 32-3 v Hastings UnitedHastings United 3-2 Chatham Town | Isthmian League - Premier Division |
| 14 | Sat 5 Oct | 31-0 v Wingate & FinchleyChatham Town 1-0 Wingate & Finchley | Isuzu FA Trophy Third Qualifying Round |
| 15 | Tue 15 Oct | 3 4-1 v Cray WanderersCray Wanderers 1-4 Chatham Town | Isthmian League - Premier Division |
| 16 | Sat 19 Oct | 32-2 v Potters Bar TownChatham Town 2-2 Potters Bar Town | Isthmian League - Premier Division |
| 17 | Sat 26 Oct | 3 1-0 v Bowers & PitseaBowers & Pitsea 0-1 Chatham Town | Isuzu FA Trophy First Round |
| 18 | Tue 29 Oct | 31-0 v Ascot UnitedAscot United 0-1 Chatham Town | Velocity Cup Third Round |
| 19 | Sat 2 Nov | 3 1-1 v LewesChatham Town 1-1 Lewes | Isthmian League - Premier Division |
| 20 | Tue 5 Nov | 31-1 v Billericay TownBillericay Town 1-1 Chatham Town | Isthmian League - Premier Division |
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