| 1 | Tue 15 Aug | 103-2 v Folkestone InvictaFolkestone Invicta 2-3 Chatham Town | Isthmian League - Premier Division |
| 2 | Sat 19 Aug | 10 2-1 v CheshuntCheshunt 1-2 Chatham Town | Isthmian League - Premier Division |
| 3 | Mon 28 Aug | 10 5-2 v Dulwich HamletDulwich Hamlet 2-5 Chatham Town | Isthmian League - Premier Division |
| 4 | Sat 2 Sep | 101-5 v RamsgateChatham Town 1-5 Ramsgate | Emirates FA Cup First Qualifying Round |
| 5 | Tue 12 Sep | 105-0 v Folkestone InvictaFolkestone Invicta 0-5 Chatham Town | Kent Senior Cup First Round |
| 6 | Sat 16 Sep | 100-0 v Potters Bar TownPotters Bar Town 0-0 Chatham Town | Isthmian League - Premier Division |
| 7 | Sat 23 Sep | 103-0 v LewesChatham Town 3-0 Lewes | Isthmian League - Premier Division |
| 8 | Tue 3 Oct | 103-1 v Tonbridge AngelsChatham Town 3-1 Tonbridge Angels | Kent Senior Cup Second Round |
| 9 | Sat 7 Oct | 10 2-1 v Heybridge SwiftsHeybridge Swifts 1-2 Chatham Town | Isuzu FA Trophy Third Qualifying Round |
| 10 | Sat 14 Oct | 102-2 v Carshalton AthleticChatham Town 2-2 Carshalton Athletic | Isthmian League - Premier Division |
| 11 | Tue 17 Oct | 10 0-2 v MargateMargate 2-0 Chatham Town | Isthmian League - Premier Division |
| 12 | Sat 21 Oct | 10 3-1 v Concord RangersConcord Rangers 1-3 Chatham Town | Isthmian League - Premier Division |
| 13 | Mon 23 Oct | 101-1 v Hashtag UnitedHashtag United 1-1 Chatham Town | Isthmian League - Premier Division |
| 14 | Sat 28 Oct | 100-2 v Cray Valley PMChatham Town 0-2 Cray Valley PM | Isuzu FA Trophy First Round |
| 15 | Tue 31 Oct | 10 4-2 v Three BridgesThree Bridges 2-4 Chatham Town | Velocity Cup Third Round |
| 16 | Sat 11 Nov | 101-0 v WhitehawkChatham Town 1-0 Whitehawk | Isthmian League - Premier Division |
| 17 | Tue 21 Nov | 102-1 v Wingate & FinchleyChatham Town 2-1 Wingate & Finchley | Isthmian League - Premier Division |
| 18 | Sat 25 Nov | 103-1 v Enfield TownChatham Town 3-1 Enfield Town | Isthmian League - Premier Division |
| 19 | Sat 2 Dec | 103-0 v Haringey BoroughHaringey Borough 0-3 Chatham Town | Isthmian League - Premier Division |
| 20 | Sat 9 Dec | 10 1-2 v Hastings UnitedChatham Town 1-2 Hastings United | Isthmian League - Premier Division |
| 21 | Tue 12 Dec | 10 2-2 v HorshamHorsham 2-2 Chatham Town | Isthmian League - Premier Division |
| 22 | Sat 16 Dec | 102-0 v HornchurchChatham Town 2-0 Hornchurch | Isthmian League - Premier Division |
| 23 | Tue 19 Dec | 103-1 v Basildon UnitedChatham Town 3-1 Basildon United | Velocity Cup Fourth Round |
| 24 | Tue 26 Dec | 103-1 v KingstonianKingstonian 1-3 Chatham Town | Isthmian League - Premier Division |
| 25 | Mon 1 Jan | 102-1 v Dulwich HamletChatham Town 2-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 26 | Sat 6 Jan | 101-2 v Bognor Regis TownBognor Regis Town 2-1 Chatham Town | Isthmian League - Premier Division |
| 27 | Sat 13 Jan | 103-2 v CheshuntChatham Town 3-2 Cheshunt | Isthmian League - Premier Division |
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