| 1 | Sat 21 Sep | 11-3 v Canvey IslandChatham Town 1-3 Canvey Island | Isthmian League - Premier Division |
| 2 | Tue 24 Sep | 11-2 v Cray WanderersChatham Town 1-2 Cray Wanderers | Kent Senior Cup First Round |
| 3 | Sat 28 Sep | 10-3 v Slough TownChatham Town 0-3 Slough Town | Emirates FA Cup Third Qualifying Round |
| 4 | Tue 1 Oct | 12-3 v Hastings UnitedHastings United 3-2 Chatham Town | Isthmian League - Premier Division |
| 5 | Sat 5 Oct | 11-0 v Wingate & FinchleyChatham Town 1-0 Wingate & Finchley | Isuzu FA Trophy Third Qualifying Round |
| 6 | Tue 15 Oct | 14-1 v Cray WanderersCray Wanderers 1-4 Chatham Town | Isthmian League - Premier Division |
| 7 | Sat 19 Oct | 12-2 v Potters Bar TownChatham Town 2-2 Potters Bar Town | Isthmian League - Premier Division |
| 8 | Sat 26 Oct | 11-0 v Bowers & PitseaBowers & Pitsea 0-1 Chatham Town | Isuzu FA Trophy First Round |
| 9 | Tue 29 Oct | 1 1-0 v Ascot UnitedAscot United 0-1 Chatham Town | Velocity Cup Third Round |
| 10 | Sat 2 Nov | 11-1 v LewesChatham Town 1-1 Lewes | Isthmian League - Premier Division |
| 11 | Tue 5 Nov | 11-1 v Billericay TownBillericay Town 1-1 Chatham Town | Isthmian League - Premier Division |
| 12 | Sat 9 Nov | 1 1-1 v Dover AthleticChatham Town 1-1 Dover Athletic | Isthmian League - Premier Division |
| 13 | Tue 12 Nov | 12-0 v HorshamChatham Town 2-0 Horsham | Isthmian League - Premier Division |
| 14 | Sat 16 Nov | 11-1 v Slough TownSlough Town 1-1 Chatham Town | Isuzu FA Trophy Second Round |
| 15 | Tue 19 Nov | 11-1 v Wingate & FinchleyWingate & Finchley 1-1 Chatham Town | Isthmian League - Premier Division |
| 16 | Sat 23 Nov | 15-0 v WhitehawkChatham Town 5-0 Whitehawk | Isthmian League - Premier Division |
| 17 | Sat 30 Nov | 17-1 v Bognor Regis TownBognor Regis Town 1-7 Chatham Town | Isthmian League - Premier Division |
| 18 | Tue 10 Dec | 11-0 v CheshuntCheshunt 0-1 Chatham Town | Isthmian League - Premier Division |
| 19 | Sat 14 Dec | 14-1 v Folkestone InvictaChatham Town 4-1 Folkestone Invicta | Isthmian League - Premier Division |
| 20 | Tue 17 Dec | 12-0 v Burgess Hill TownChatham Town 2-0 Burgess Hill Town | Velocity Cup Fourth Round |
| 21 | Sat 21 Dec | 10-2 v Carshalton AthleticCarshalton Athletic 2-0 Chatham Town | Isthmian League - Premier Division |
| 22 | Thu 26 Dec | 13-3 v Cray Valley PMCray Valley PM 3-3 Chatham Town | Isthmian League - Premier Division |
| 23 | Sat 28 Dec | 13-1 v Bowers & PitseaChatham Town 3-1 Bowers & Pitsea | Isthmian League - Premier Division |
| 24 | Wed 1 Jan | 10-2 v DartfordChatham Town 0-2 Dartford | Isthmian League - Premier Division |
| 25 | Sat 4 Jan | 10-2 v Chichester CityChichester City 2-0 Chatham Town | Isthmian League - Premier Division |
| 26 | Tue 7 Jan | 10-1 v Hashtag UnitedChatham Town 0-1 Hashtag United | Isthmian League - Premier Division |
| 27 | Sat 11 Jan | 13-1 v Wingate & FinchleyChatham Town 3-1 Wingate & Finchley | Isthmian League - Premier Division |
| 28 | Sun 19 Jan | 10-1 v Potters Bar TownPotters Bar Town 1-0 Chatham Town | Isthmian League - Premier Division |
| 29 | Tue 28 Jan | 13-2 v Hashtag UnitedHashtag United 2-3 Chatham Town | Velocity Cup Quarter Final |
| 30 | Sat 1 Feb | 10-1 v Canvey IslandCanvey Island 1-0 Chatham Town | Isthmian League - Premier Division |
| 31 | Sat 8 Feb | 11-4 v Cray WanderersChatham Town 1-4 Cray Wanderers | Isthmian League - Premier Division |
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