| 1 | Sat 13 Aug 2016 | 40-0 v Three BridgesThree Bridges 0-0 Chatham Town | Ryman League Division One South |
| 2 | Mon 15 Aug 2016 | 72-3 v Tooting & Mitcham UnitedChatham Town 2-3 Tooting & Mitcham United | Ryman League Division One South |
| 3 | Mon 5 Sep 2016 | 83-2 v Herne BayChatham Town 3-2 Herne Bay | Ryman League Division One South |
| 4 | Sat 10 Sep 2016 | 42-3 v East Grinstead TownChatham Town 2-3 East Grinstead Town | Ryman League Division One South |
| 5 | Mon 12 Sep 2016 | 71-0 v VCD AthleticChatham Town 1-0 VCD Athletic | Alan Turvey Trophy First Round |
| 6 | Mon 19 Sep 2016 | 82-3 v WhyteleafeChatham Town 2-3 Whyteleafe | Ryman League Division One South |
| 7 | Sat 24 Sep 2016 | 40-3 v Greenwich BoroughGreenwich Borough 3-0 Chatham Town | Ryman League Division One South |
| 8 | Tue 27 Sep 2016 | 81-7 v Faversham TownFaversham Town 7-1 Chatham Town | Ryman League Division One South |
| 9 | Sat 1 Oct 2016 | 80-1 v South ParkChatham Town 0-1 South Park | Ryman League Division One South |
| 10 | Sat 8 Oct 2016 | 41-4 v Aylesbury UnitedAylesbury United 4-1 Chatham Town | FA Trophy Preliminary Round |
| 11 | Mon 10 Oct 2016 | 75-2 v RamsgateChatham Town 5-2 Ramsgate | Ryman League Division One South |
| 12 | Wed 19 Oct 2016 | 80-1 v RomfordRomford 1-0 Chatham Town | Alan Turvey Trophy Second Round |
| 13 | Sat 22 Oct 2016 | 71-4 v Corinthian-CasualsChatham Town 1-4 Corinthian-Casuals | Ryman League Division One South |
| 14 | Sat 29 Oct 2016 | 71-2 v Carshalton AthleticChatham Town 1-2 Carshalton Athletic | Ryman League Division One South |
| 15 | Tue 1 Nov 2016 | 73-4 v Tooting & Mitcham UnitedTooting & Mitcham United 4-3 Chatham Town | Ryman League Division One South |
| 16 | Sat 5 Nov 2016 | 82-2 v SittingbourneSittingbourne 2-2 Chatham Town | Ryman League Division One South |
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