| 1 | Sat 3 Aug | 53-2 v Herne BayHerne Bay 2-3 Chatham Town | Friendly |
| 2 | Sat 21 Sep | 5 1-3 v Canvey IslandChatham Town 1-3 Canvey Island | Isthmian League - Premier Division |
| 3 | Tue 24 Sep | 51-2 v Cray WanderersChatham Town 1-2 Cray Wanderers | Kent Senior Cup First Round |
| 4 | Tue 1 Oct | 52-3 v Hastings UnitedHastings United 3-2 Chatham Town | Isthmian League - Premier Division |
| 5 | Sat 5 Oct | 51-0 v Wingate & FinchleyChatham Town 1-0 Wingate & Finchley | Isuzu FA Trophy Third Qualifying Round |
| 6 | Tue 15 Oct | 54-1 v Cray WanderersCray Wanderers 1-4 Chatham Town | Isthmian League - Premier Division |
| 7 | Sat 19 Oct | 52-2 v Potters Bar TownChatham Town 2-2 Potters Bar Town | Isthmian League - Premier Division |
| 8 | Sat 26 Oct | 51-0 v Bowers & PitseaBowers & Pitsea 0-1 Chatham Town | Isuzu FA Trophy First Round |
| 9 | Sat 2 Nov | 51-1 v LewesChatham Town 1-1 Lewes | Isthmian League - Premier Division |
| 10 | Tue 5 Nov | 51-1 v Billericay TownBillericay Town 1-1 Chatham Town | Isthmian League - Premier Division |
| 11 | Sat 9 Nov | 51-1 v Dover AthleticChatham Town 1-1 Dover Athletic | Isthmian League - Premier Division |
| 12 | Tue 12 Nov | 5 2-0 v HorshamChatham Town 2-0 Horsham | Isthmian League - Premier Division |
| 13 | Sat 16 Nov | 51-1 v Slough TownSlough Town 1-1 Chatham Town | Isuzu FA Trophy Second Round |
| 14 | Tue 19 Nov | 51-1 v Wingate & FinchleyWingate & Finchley 1-1 Chatham Town | Isthmian League - Premier Division |
| 15 | Sat 23 Nov | 5 5-0 v WhitehawkChatham Town 5-0 Whitehawk | Isthmian League - Premier Division |
| 16 | Sat 30 Nov | 57-1 v Bognor Regis TownBognor Regis Town 1-7 Chatham Town | Isthmian League - Premier Division |
| 17 | Tue 10 Dec | 51-0 v CheshuntCheshunt 0-1 Chatham Town | Isthmian League - Premier Division |
| 18 | Sat 14 Dec | 54-1 v Folkestone InvictaChatham Town 4-1 Folkestone Invicta | Isthmian League - Premier Division |
| 19 | Wed 1 Jan | 50-2 v DartfordChatham Town 0-2 Dartford | Isthmian League - Premier Division |
| 20 | Tue 7 Jan | 50-1 v Hashtag UnitedChatham Town 0-1 Hashtag United | Isthmian League - Premier Division |
| 21 | Tue 28 Jan | 53-2 v Hashtag UnitedHashtag United 2-3 Chatham Town | Velocity Cup Quarter Final |
| 22 | Sat 1 Feb | 50-1 v Canvey IslandCanvey Island 1-0 Chatham Town | Isthmian League - Premier Division |
| 23 | Sat 8 Feb | 5 1-4 v Cray WanderersChatham Town 1-4 Cray Wanderers | Isthmian League - Premier Division |
| 24 | Sat 15 Feb | 51-1 v HorshamHorsham 1-1 Chatham Town | Isthmian League - Premier Division |
| 25 | Sat 1 Mar | 54-1 v CheshuntChatham Town 4-1 Cheshunt | Isthmian League - Premier Division |
| 26 | Tue 4 Mar | 52-0 v Hastings UnitedChatham Town 2-0 Hastings United | Isthmian League - Premier Division |
| 27 | Sat 8 Mar | 52-0 v WhitehawkWhitehawk 0-2 Chatham Town | Isthmian League - Premier Division |
| 28 | Tue 11 Mar | 52-1 v HendonChatham Town 2-1 Hendon | Velocity Cup Semi Final |
| 29 | Sat 15 Mar | 51-1 v Bognor Regis TownChatham Town 1-1 Bognor Regis Town | Isthmian League - Premier Division |
| 30 | Sat 22 Mar | 51-0 v Hashtag UnitedHashtag United 0-1 Chatham Town | Isthmian League - Premier Division |
| 31 | Sat 29 Mar | 5 3-1 v Folkestone InvictaFolkestone Invicta 1-3 Chatham Town | Isthmian League - Premier Division |
| 32 | Sat 5 Apr | 53-0 v Carshalton AthleticChatham Town 3-0 Carshalton Athletic | Isthmian League - Premier Division |
| 33 | Wed 9 Apr | 5 2-3 v Billericay TownBillericay Town 3-2 Chatham Town | Velocity Cup Final |
| 34 | Sat 12 Apr | 50-1 v Chichester CityChatham Town 0-1 Chichester City | Isthmian League - Premier Division |
| 35 | Sat 19 Apr | 5 3-3 v HendonHendon 3-3 Chatham Town | Isthmian League - Premier Division |
| 36 | Mon 21 Apr | 5 0-1 v Cray Valley PMChatham Town 0-1 Cray Valley PM | Isthmian League - Premier Division |
| 37 | Sat 26 Apr | 52-2 v Dulwich HamletDulwich Hamlet 2-2 Chatham Town | Isthmian League - Premier Division |
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