| 1 | Sat 9 Sep | 51-5 v Cray WanderersChatham Town 1-5 Cray Wanderers | Isthmian League - Premier Division |
| 2 | Tue 12 Sep | 55-0 v Folkestone InvictaFolkestone Invicta 0-5 Chatham Town | Kent Senior Cup First Round |
| 3 | Sat 16 Sep | 50-0 v Potters Bar TownPotters Bar Town 0-0 Chatham Town | Isthmian League - Premier Division |
| 4 | Sat 23 Sep | 53-0 v LewesChatham Town 3-0 Lewes | Isthmian League - Premier Division |
| 5 | Sat 7 Oct | 52-1 v Heybridge SwiftsHeybridge Swifts 1-2 Chatham Town | Isuzu FA Trophy Third Qualifying Round |
| 6 | Sat 14 Oct | 52-2 v Carshalton AthleticChatham Town 2-2 Carshalton Athletic | Isthmian League - Premier Division |
| 7 | Tue 17 Oct | 50-2 v MargateMargate 2-0 Chatham Town | Isthmian League - Premier Division |
| 8 | Sat 21 Oct | 53-1 v Concord RangersConcord Rangers 1-3 Chatham Town | Isthmian League - Premier Division |
| 9 | Mon 23 Oct | 51-1 v Hashtag UnitedHashtag United 1-1 Chatham Town | Isthmian League - Premier Division |
| 10 | Sat 28 Oct | 50-2 v Cray Valley PMChatham Town 0-2 Cray Valley PM | Isuzu FA Trophy First Round |
| 11 | Tue 31 Oct | 54-2 v Three BridgesThree Bridges 2-4 Chatham Town | Velocity Cup Third Round |
| 12 | Tue 7 Nov | 5 0-2 v Billericay TownBillericay Town 2-0 Chatham Town | Isthmian League - Premier Division |
| 13 | Sat 11 Nov | 51-0 v WhitehawkChatham Town 1-0 Whitehawk | Isthmian League - Premier Division |
| 14 | Tue 21 Nov | 5 2-1 v Wingate & FinchleyChatham Town 2-1 Wingate & Finchley | Isthmian League - Premier Division |
| 15 | Sat 25 Nov | 53-1 v Enfield TownChatham Town 3-1 Enfield Town | Isthmian League - Premier Division |
| 16 | Tue 28 Nov | 52-3 v Canvey IslandCanvey Island 3-2 Chatham Town | Isthmian League - Premier Division |
| 17 | Sat 2 Dec | 53-0 v Haringey BoroughHaringey Borough 0-3 Chatham Town | Isthmian League - Premier Division |
| 18 | Sat 9 Dec | 5 1-2 v Hastings UnitedChatham Town 1-2 Hastings United | Isthmian League - Premier Division |
| 19 | Tue 12 Dec | 52-2 v HorshamHorsham 2-2 Chatham Town | Isthmian League - Premier Division |
| 20 | Sat 16 Dec | 52-0 v HornchurchChatham Town 2-0 Hornchurch | Isthmian League - Premier Division |
| 21 | Tue 26 Dec | 53-1 v KingstonianKingstonian 1-3 Chatham Town | Isthmian League - Premier Division |
| 22 | Mon 1 Jan | 52-1 v Dulwich HamletChatham Town 2-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 23 | Sat 6 Jan | 51-2 v Bognor Regis TownBognor Regis Town 2-1 Chatham Town | Isthmian League - Premier Division |
| 24 | Sat 13 Jan | 53-2 v CheshuntChatham Town 3-2 Cheshunt | Isthmian League - Premier Division |
| 25 | Sat 27 Jan | 55-1 v Canvey IslandChatham Town 5-1 Canvey Island | Isthmian League - Premier Division |
| 26 | Tue 30 Jan | 52-3 v Hashtag UnitedChatham Town 2-3 Hashtag United | Isthmian League - Premier Division |
| 27 | Sat 3 Feb | 52-1 v WhitehawkWhitehawk 1-2 Chatham Town | Isthmian League - Premier Division |
| 28 | Tue 6 Feb | 52-4 v Wingate & FinchleyWingate & Finchley 4-2 Chatham Town | Isthmian League - Premier Division |
| 29 | Sat 10 Feb | 52-1 v MargateChatham Town 2-1 Margate | Isthmian League - Premier Division |
| 30 | Sat 17 Feb | 5 3-0 v LewesLewes 0-3 Chatham Town | Isthmian League - Premier Division |
| 31 | Tue 20 Feb | 57-2 v Hythe TownChatham Town 7-2 Hythe Town | Kent Senior Cup Quarter Final |
| 32 | Sat 24 Feb | 56-3 v Billericay TownChatham Town 6-3 Billericay Town | Isthmian League - Premier Division |
| 33 | Sat 2 Mar | 50-2 v Carshalton AthleticCarshalton Athletic 2-0 Chatham Town | Isthmian League - Premier Division |
| 34 | Tue 19 Mar | 53-5 v Ebbsfleet UnitedEbbsfleet United 5-3 Chatham Town | Kent Senior Cup Semi Final |
| 35 | Sat 23 Mar | 5 2-1 v Haringey BoroughChatham Town 2-1 Haringey Borough | Isthmian League - Premier Division |
| 36 | Fri 29 Mar | 52-2 v Cray WanderersCray Wanderers 2-2 Chatham Town | Isthmian League - Premier Division |
| 37 | Mon 1 Apr | 54-1 v KingstonianChatham Town 4-1 Kingstonian | Isthmian League - Premier Division |
| 38 | Sat 6 Apr | 51-2 v HornchurchHornchurch 2-1 Chatham Town | Isthmian League - Premier Division |
| 39 | Sat 13 Apr | 5 2-0 v Folkestone InvictaChatham Town 2-0 Folkestone Invicta | Isthmian League - Premier Division |
| 40 | Wed 17 Apr | 52-1 v Hashtag UnitedChatham Town 2-1 Hashtag United | Velocity Cup Final |
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