| 1 | Sat 9 Aug | 50-0 v St Albans CitySt Albans City 0-0 Chatham Town | Isthmian League - Premier Division |
| 2 | Tue 12 Aug | 54-2 v RamsgateChatham Town 4-2 Ramsgate | Isthmian League - Premier Division |
| 3 | Sat 16 Aug | 51-0 v CheshuntChatham Town 1-0 Cheshunt | Isthmian League - Premier Division |
| 4 | Sat 23 Aug | 52-0 v AveleyAveley 0-2 Chatham Town | Isthmian League - Premier Division |
| 5 | Mon 25 Aug | 51-2 v Folkestone InvictaChatham Town 1-2 Folkestone Invicta | Isthmian League - Premier Division |
| 6 | Sat 6 Sep | 53-0 v Wingate & FinchleyWingate & Finchley 0-3 Chatham Town | Isthmian League - Premier Division |
| 7 | Sat 13 Sep | 53-0 v Ashford UnitedAshford United 0-3 Chatham Town | Emirates FA Cup Second Qualifying Round |
| 8 | Tue 16 Sep | 5 3-1 v Cray Valley PMChatham Town 3-1 Cray Valley PM | Isthmian League - Premier Division |
| 9 | Sat 20 Sep | 52-1 v Carshalton AthleticChatham Town 2-1 Carshalton Athletic | Isthmian League - Premier Division |
| 10 | Sat 27 Sep | 53-1 v Deal TownChatham Town 3-1 Deal Town | Emirates FA Cup Third Qualifying Round |
| 11 | Sat 4 Oct | 50-0 v Needham MarketChatham Town 0-0 Needham Market | Isuzu FA Trophy Third Qualifying Round |
| 12 | Sat 11 Oct | 53-1 v Tonbridge AngelsTonbridge Angels 1-3 Chatham Town | Emirates FA Cup Fourth Qualifying Round |
| 13 | Tue 14 Oct | 51-0 v Cray Valley PMCray Valley PM 0-1 Chatham Town | Isthmian League - Premier Division |
| 14 | Sat 18 Oct | 53-3 v Cray WanderersChatham Town 3-3 Cray Wanderers | Isthmian League - Premier Division |
| 15 | Tue 21 Oct | 50-0 v Dulwich HamletChatham Town 0-0 Dulwich Hamlet | Isthmian League - Premier Division |
| 16 | Sat 25 Oct | 52-0 v Waltham AbbeyWaltham Abbey 0-2 Chatham Town | Isuzu FA Trophy First Round |
| 17 | Sat 1 Nov | 51-2 v BuxtonBuxton 2-1 Chatham Town | Emirates FA Cup First Round |
| 18 | Tue 4 Nov | 5 1-2 v Billericay TownBillericay Town 2-1 Chatham Town | Isthmian League - Premier Division |
| 19 | Sat 8 Nov | 56-0 v Hashtag UnitedHashtag United 0-6 Chatham Town | Isthmian League - Premier Division |
| 20 | Tue 11 Nov | 50-1 v RamsgateRamsgate 1-0 Chatham Town | Isthmian League - Premier Division |
| 21 | Sat 15 Nov | 51-0 v Wimborne TownWimborne Town 0-1 Chatham Town | Isuzu FA Trophy Second Round |
| 22 | Sat 22 Nov | 5 2-0 v LewesLewes 0-2 Chatham Town | Isthmian League - Premier Division |
| 23 | Tue 25 Nov | 51-0 v Welling UnitedWelling United 0-1 Chatham Town | Isthmian League - Premier Division |
| 24 | Sat 29 Nov | 51-4 v St Albans CityChatham Town 1-4 St Albans City | Isthmian League - Premier Division |
| 25 | Tue 2 Dec | 52-2 v Chichester CityChichester City 2-2 Chatham Town | Isthmian League - Premier Division |
| 26 | Sat 6 Dec | 54-0 v Burgess Hill TownChatham Town 4-0 Burgess Hill Town | Isthmian League - Premier Division |
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