| 1 | Sat 21 Oct | 163-1 v Concord RangersConcord Rangers 1-3 Chatham Town | Isthmian League - Premier Division |
| 2 | Mon 23 Oct | 161-1 v Hashtag UnitedHashtag United 1-1 Chatham Town | Isthmian League - Premier Division |
| 3 | Sat 28 Oct | 160-2 v Cray Valley PMChatham Town 0-2 Cray Valley PM | Isuzu FA Trophy First Round |
| 4 | Tue 31 Oct | 164-2 v Three BridgesThree Bridges 2-4 Chatham Town | Velocity Cup Third Round |
| 5 | Tue 7 Nov | 160-2 v Billericay TownBillericay Town 2-0 Chatham Town | Isthmian League - Premier Division |
| 6 | Tue 21 Nov | 162-1 v Wingate & FinchleyChatham Town 2-1 Wingate & Finchley | Isthmian League - Premier Division |
| 7 | Sat 25 Nov | 163-1 v Enfield TownChatham Town 3-1 Enfield Town | Isthmian League - Premier Division |
| 8 | Tue 19 Dec | 163-1 v Basildon UnitedChatham Town 3-1 Basildon United | Velocity Cup Fourth Round |
| 9 | Tue 26 Dec | 163-1 v KingstonianKingstonian 1-3 Chatham Town | Isthmian League - Premier Division |
| 10 | Mon 1 Jan | 162-1 v Dulwich HamletChatham Town 2-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 11 | Sat 6 Jan | 161-2 v Bognor Regis TownBognor Regis Town 2-1 Chatham Town | Isthmian League - Premier Division |
| 12 | Sat 13 Jan | 163-2 v CheshuntChatham Town 3-2 Cheshunt | Isthmian League - Premier Division |
| 13 | Sat 27 Jan | 16 5-1 v Canvey IslandChatham Town 5-1 Canvey Island | Isthmian League - Premier Division |
| 14 | Sat 3 Feb | 162-1 v WhitehawkWhitehawk 1-2 Chatham Town | Isthmian League - Premier Division |
| 15 | Tue 6 Feb | 162-4 v Wingate & FinchleyWingate & Finchley 4-2 Chatham Town | Isthmian League - Premier Division |
| 16 | Sat 10 Feb | 162-1 v MargateChatham Town 2-1 Margate | Isthmian League - Premier Division |
| 17 | Tue 13 Feb | 161-1 v Billericay TownBillericay Town 1-1 Chatham Town | Velocity Cup Quarter Final |
| 18 | Sat 17 Feb | 163-0 v LewesLewes 0-3 Chatham Town | Isthmian League - Premier Division |
| 19 | Tue 20 Feb | 167-2 v Hythe TownChatham Town 7-2 Hythe Town | Kent Senior Cup Quarter Final |
| 20 | Sat 24 Feb | 166-3 v Billericay TownChatham Town 6-3 Billericay Town | Isthmian League - Premier Division |
| 21 | Sat 2 Mar | 160-2 v Carshalton AthleticCarshalton Athletic 2-0 Chatham Town | Isthmian League - Premier Division |
| 22 | Sat 9 Mar | 162-1 v Concord RangersChatham Town 2-1 Concord Rangers | Isthmian League - Premier Division |
| 23 | Tue 12 Mar | 164-2 v Ashford UnitedChatham Town 4-2 Ashford United | Velocity Cup Semi Final |
| 24 | Sat 16 Mar | 161-1 v Hastings UnitedHastings United 1-1 Chatham Town | Isthmian League - Premier Division |
| 25 | Tue 19 Mar | 163-5 v Ebbsfleet UnitedEbbsfleet United 5-3 Chatham Town | Kent Senior Cup Semi Final |
| 26 | Sat 23 Mar | 162-1 v Haringey BoroughChatham Town 2-1 Haringey Borough | Isthmian League - Premier Division |
| 27 | Mon 1 Apr | 164-1 v KingstonianChatham Town 4-1 Kingstonian | Isthmian League - Premier Division |
| 28 | Sat 6 Apr | 161-2 v HornchurchHornchurch 2-1 Chatham Town | Isthmian League - Premier Division |
| 29 | Sat 13 Apr | 162-0 v Folkestone InvictaChatham Town 2-0 Folkestone Invicta | Isthmian League - Premier Division |
| 30 | Wed 17 Apr | 16 2-1 v Hashtag UnitedChatham Town 2-1 Hashtag United | Velocity Cup Final |
| 31 | Sat 20 Apr | 161-3 v HorshamChatham Town 1-3 Horsham | Isthmian League - Premier Division |
| 32 | Sat 27 Apr | 162-2 v Enfield TownEnfield Town 2-2 Chatham Town | Isthmian League - Premier Division |
| 33 | Wed 1 May | 161-1 v HorshamChatham Town 1-1 Horsham | Isthmian League - Premier Division Play-off Semi Final |
| 34 | Mon 6 May | 160-3 v Enfield TownChatham Town 0-3 Enfield Town | Isthmian League - Premier Division Play-off Final |
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