| 1 | Sat 12 Aug | 31-0 v Bognor Regis TownChatham Town 1-0 Bognor Regis Town | Isthmian League - Premier Division |
| 2 | Tue 15 Aug | 33-2 v Folkestone InvictaFolkestone Invicta 2-3 Chatham Town | Isthmian League - Premier Division |
| 3 | Sat 19 Aug | 3 2-1 v CheshuntCheshunt 1-2 Chatham Town | Isthmian League - Premier Division |
| 4 | Sat 26 Aug | 32-0 v Potters Bar TownChatham Town 2-0 Potters Bar Town | Isthmian League - Premier Division |
| 5 | Mon 28 Aug | 35-2 v Dulwich HamletDulwich Hamlet 2-5 Chatham Town | Isthmian League - Premier Division |
| 6 | Sat 2 Sep | 3 1-5 v RamsgateChatham Town 1-5 Ramsgate | Emirates FA Cup First Qualifying Round |
| 7 | Sat 9 Sep | 111-3 v Spartans YouthSpartans Youth 3-1 Langley | Combined Counties League Division One |
| 8 | Sat 9 Sep | 31-5 v Cray WanderersChatham Town 1-5 Cray Wanderers | Isthmian League - Premier Division |
| 9 | Tue 12 Sep | 35-0 v Folkestone InvictaFolkestone Invicta 0-5 Chatham Town | Kent Senior Cup First Round |
| 10 | Wed 13 Sep | 152-1 v WestsideWestside 1-2 Langley | Combined Counties League Division One |
| 11 | Sat 16 Sep | 30-0 v Potters Bar TownPotters Bar Town 0-0 Chatham Town | Isthmian League - Premier Division |
| 12 | Sat 23 Sep | 33-0 v LewesChatham Town 3-0 Lewes | Isthmian League - Premier Division |
| 13 | Sat 30 Sep | 111-1 v Eversley & CaliforniaEversley & California 1-1 Langley | Combined Counties League Division One |
| 14 | Tue 3 Oct | 33-1 v Tonbridge AngelsChatham Town 3-1 Tonbridge Angels | Kent Senior Cup Second Round |
| 15 | Sat 7 Oct | 32-1 v Heybridge SwiftsHeybridge Swifts 1-2 Chatham Town | Isuzu FA Trophy Third Qualifying Round |
| 16 | Sat 14 Oct | 3 2-2 v Carshalton AthleticChatham Town 2-2 Carshalton Athletic | Isthmian League - Premier Division |
| 17 | Tue 17 Oct | 30-2 v MargateMargate 2-0 Chatham Town | Isthmian League - Premier Division |
| 18 | Sat 21 Oct | 33-1 v Concord RangersConcord Rangers 1-3 Chatham Town | Isthmian League - Premier Division |
| 19 | Mon 23 Oct | 31-1 v Hashtag UnitedHashtag United 1-1 Chatham Town | Isthmian League - Premier Division |
| 20 | Sat 28 Oct | 152-4 v Woodley UnitedWoodley United 4-2 Langley | Combined Counties League Division One |
| 21 | Wed 1 Nov | 140-1 v FC Deportivo GaliciaLangley 0-1 FC Deportivo Galicia | Combined Counties League Division One |
| 22 | Tue 7 Nov | 30-2 v Billericay TownBillericay Town 2-0 Chatham Town | Isthmian League - Premier Division |
| 23 | Sat 11 Nov | 3 1-0 v WhitehawkChatham Town 1-0 Whitehawk | Isthmian League - Premier Division |
| 24 | Tue 21 Nov | 32-1 v Wingate & FinchleyChatham Town 2-1 Wingate & Finchley | Isthmian League - Premier Division |
| 25 | Sat 25 Nov | 33-1 v Enfield TownChatham Town 3-1 Enfield Town | Isthmian League - Premier Division |
| 26 | Tue 28 Nov | 32-3 v Canvey IslandCanvey Island 3-2 Chatham Town | Isthmian League - Premier Division |
| 27 | Sat 9 Dec | 31-2 v Hastings UnitedChatham Town 1-2 Hastings United | Isthmian League - Premier Division |
| 28 | Tue 12 Dec | 32-2 v HorshamHorsham 2-2 Chatham Town | Isthmian League - Premier Division |
| 29 | Wed 13 Dec | 121-1 v Oxhey JetsLangley 1-1 Oxhey Jets | Combined Counties League Division One |
| 30 | Tue 30 Jan | 172-3 v Hashtag UnitedChatham Town 2-3 Hashtag United | Isthmian League - Premier Division |
| 31 | Sat 3 Feb | 32-1 v WhitehawkWhitehawk 1-2 Chatham Town | Isthmian League - Premier Division |
| 32 | Tue 6 Feb | 32-4 v Wingate & FinchleyWingate & Finchley 4-2 Chatham Town | Isthmian League - Premier Division |
| 33 | Sat 2 Mar | 144-3 v WestsideLangley 4-3 Westside | Combined Counties League Division One |
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