| 1 | Sat 13 Aug 2016 | 10-0 v Three BridgesThree Bridges 0-0 Chatham Town | Ryman League Division One South |
| 2 | Mon 15 Aug 2016 | 12-3 v Tooting & Mitcham UnitedChatham Town 2-3 Tooting & Mitcham United | Ryman League Division One South |
| 3 | Sat 20 Aug 2016 | 13-3 v Walton CasualsWalton Casuals 3-3 Chatham Town | Emirates FA Cup Preliminary Round |
| 4 | Mon 22 Aug 2016 | 11-2 v Walton CasualsChatham Town 1-2 Walton Casuals | Emirates FA Cup Preliminary Round Replay |
| 5 | Mon 29 Aug 2016 | 11-3 v Cray WanderersChatham Town 1-3 Cray Wanderers | Ryman League Division One South |
| 6 | Mon 5 Sep 2016 | 13-2 v Herne BayChatham Town 3-2 Herne Bay | Ryman League Division One South |
| 7 | Sat 10 Sep 2016 | 12-3 v East Grinstead TownChatham Town 2-3 East Grinstead Town | Ryman League Division One South |
| 8 | Mon 19 Sep 2016 | 12-3 v WhyteleafeChatham Town 2-3 Whyteleafe | Ryman League Division One South |
| 9 | Sat 24 Sep 2016 | 10-3 v Greenwich BoroughGreenwich Borough 3-0 Chatham Town | Ryman League Division One South |
| 10 | Sat 1 Oct 2016 | 10-1 v South ParkChatham Town 0-1 South Park | Ryman League Division One South |
| 11 | Sat 8 Oct 2016 | 11-4 v Aylesbury UnitedAylesbury United 4-1 Chatham Town | FA Trophy Preliminary Round |
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