| 1 | Sat 3 Aug | 73-2 v Herne BayHerne Bay 2-3 Chatham Town | Friendly |
| 2 | Sat 10 Aug | 7 0-2 v LewesLewes 2-0 Chatham Town | Isthmian League - Premier Division |
| 3 | Tue 13 Aug | 71-1 v Billericay TownChatham Town 1-1 Billericay Town | Isthmian League - Premier Division |
| 4 | Sat 17 Aug | 72-0 v Bowers & PitseaBowers & Pitsea 0-2 Chatham Town | Isthmian League - Premier Division |
| 5 | Sat 31 Aug | 72-0 v WestfieldWestfield 0-2 Chatham Town | Emirates FA Cup First Qualifying Round |
| 6 | Sat 7 Sep | 72-2 v HendonChatham Town 2-2 Hendon | Isthmian League - Premier Division |
| 7 | Sat 14 Sep | 7 1-0 v Welling UnitedWelling United 0-1 Chatham Town | Emirates FA Cup Second Qualifying Round |
| 8 | Sat 21 Sep | 7 1-3 v Canvey IslandChatham Town 1-3 Canvey Island | Isthmian League - Premier Division |
| 9 | Sat 28 Sep | 70-3 v Slough TownChatham Town 0-3 Slough Town | Emirates FA Cup Third Qualifying Round |
| 10 | Tue 1 Oct | 7 2-3 v Hastings UnitedHastings United 3-2 Chatham Town | Isthmian League - Premier Division |
| 11 | Sat 5 Oct | 7 1-0 v Wingate & FinchleyChatham Town 1-0 Wingate & Finchley | Isuzu FA Trophy Third Qualifying Round |
| 12 | Sat 19 Oct | 7 2-2 v Potters Bar TownChatham Town 2-2 Potters Bar Town | Isthmian League - Premier Division |
| 13 | Sat 26 Oct | 71-0 v Bowers & PitseaBowers & Pitsea 0-1 Chatham Town | Isuzu FA Trophy First Round |
| 14 | Tue 5 Nov | 7 1-1 v Billericay TownBillericay Town 1-1 Chatham Town | Isthmian League - Premier Division |
| 15 | Sat 9 Nov | 71-1 v Dover AthleticChatham Town 1-1 Dover Athletic | Isthmian League - Premier Division |
| 16 | Tue 12 Nov | 72-0 v HorshamChatham Town 2-0 Horsham | Isthmian League - Premier Division |
| 17 | Sat 16 Nov | 71-1 v Slough TownSlough Town 1-1 Chatham Town | Isuzu FA Trophy Second Round |
| 18 | Tue 19 Nov | 71-1 v Wingate & FinchleyWingate & Finchley 1-1 Chatham Town | Isthmian League - Premier Division |
| 19 | Sat 23 Nov | 75-0 v WhitehawkChatham Town 5-0 Whitehawk | Isthmian League - Premier Division |
| 20 | Sat 30 Nov | 77-1 v Bognor Regis TownBognor Regis Town 1-7 Chatham Town | Isthmian League - Premier Division |
| 21 | Tue 10 Dec | 71-0 v CheshuntCheshunt 0-1 Chatham Town | Isthmian League - Premier Division |
| 22 | Sat 14 Dec | 74-1 v Folkestone InvictaChatham Town 4-1 Folkestone Invicta | Isthmian League - Premier Division |
| 23 | Tue 17 Dec | 7 2-0 v Burgess Hill TownChatham Town 2-0 Burgess Hill Town | Velocity Cup Fourth Round |
| 24 | Sat 21 Dec | 70-2 v Carshalton AthleticCarshalton Athletic 2-0 Chatham Town | Isthmian League - Premier Division |
| 25 | Thu 26 Dec | 7 3-3 v Cray Valley PMCray Valley PM 3-3 Chatham Town | Isthmian League - Premier Division |
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