| 1 | Sat 10 Sep 2016 | 32-3 v East Grinstead TownChatham Town 2-3 East Grinstead Town | Ryman League Division One South |
| 2 | Mon 19 Sep 2016 | 32-3 v WhyteleafeChatham Town 2-3 Whyteleafe | Ryman League Division One South |
| 3 | Sat 24 Sep 2016 | 30-3 v Greenwich BoroughGreenwich Borough 3-0 Chatham Town | Ryman League Division One South |
| 4 | Sat 1 Oct 2016 | 30-1 v South ParkChatham Town 0-1 South Park | Ryman League Division One South |
| 5 | Sat 8 Oct 2016 | 31-4 v Aylesbury UnitedAylesbury United 4-1 Chatham Town | FA Trophy Preliminary Round |
| 6 | Wed 19 Oct 2016 | 170-1 v RomfordRomford 1-0 Chatham Town | Alan Turvey Trophy Second Round |
| 7 | Sat 22 Oct 2016 | 31-4 v Corinthian-CasualsChatham Town 1-4 Corinthian-Casuals | Ryman League Division One South |
| 8 | Tue 1 Nov 2016 | 153-4 v Tooting & Mitcham UnitedTooting & Mitcham United 4-3 Chatham Town | Ryman League Division One South |
| 9 | Sat 5 Nov 2016 | 32-2 v SittingbourneSittingbourne 2-2 Chatham Town | Ryman League Division One South |
| 10 | Sat 19 Nov 2016 | 30-7 v Hastings UnitedChatham Town 0-7 Hastings United | Ryman League Division One South |
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