| 1 | Mon 10 Oct 2016 | 15-2 v RamsgateChatham Town 5-2 Ramsgate | Ryman League Division One South |
| 2 | Sat 15 Oct 2016 | 12-1 v Dorking WanderersDorking Wanderers 1-2 Chatham Town | Ryman League Division One South |
| 3 | Wed 19 Oct 2016 | 10-1 v RomfordRomford 1-0 Chatham Town | Alan Turvey Trophy Second Round |
| 4 | Sat 22 Oct 2016 | 11-4 v Corinthian-CasualsChatham Town 1-4 Corinthian-Casuals | Ryman League Division One South |
| 5 | Sat 29 Oct 2016 | 11-2 v Carshalton AthleticChatham Town 1-2 Carshalton Athletic | Ryman League Division One South |
| 6 | Tue 1 Nov 2016 | 13-4 v Tooting & Mitcham UnitedTooting & Mitcham United 4-3 Chatham Town | Ryman League Division One South |
| 7 | Sat 5 Nov 2016 | 12-2 v SittingbourneSittingbourne 2-2 Chatham Town | Ryman League Division One South |
| 8 | Sat 19 Nov 2016 | 10-7 v Hastings UnitedChatham Town 0-7 Hastings United | Ryman League Division One South |
| 9 | Tue 29 Nov 2016 | 11-0 v WhyteleafeWhyteleafe 0-1 Chatham Town | Ryman League Division One South |
| 10 | Sat 3 Dec 2016 | 10-3 v Greenwich BoroughChatham Town 0-3 Greenwich Borough | Ryman League Division One South |
| 11 | Sat 17 Dec 2016 | 11-4 v Walton CasualsChatham Town 1-4 Walton Casuals | Ryman League Division One South |
| 12 | Tue 27 Dec 2016 | 11-3 v Hythe TownChatham Town 1-3 Hythe Town | Ryman League Division One South |
| 13 | Fri 30 Dec 2016 | 11-2 v Herne BayHerne Bay 2-1 Chatham Town | Ryman League Division One South |
| 14 | Mon 2 Jan 2017 | 10-3 v Cray WanderersCray Wanderers 3-0 Chatham Town | Ryman League Division One South |
| 15 | Sat 7 Jan 2017 | 14-4 v ChipsteadChatham Town 4-4 Chipstead | Ryman League Division One South |
| 16 | Sat 14 Jan 2017 | 11-6 v Carshalton AthleticCarshalton Athletic 6-1 Chatham Town | Ryman League Division One South |
| 17 | Mon 16 Jan 2017 | 10-1 v Faversham TownChatham Town 0-1 Faversham Town | Ryman League Division One South |
| 18 | Sat 28 Jan 2017 | 11-2 v RamsgateRamsgate 2-1 Chatham Town | Ryman League Division One South |
| 19 | Sat 4 Feb 2017 | 11-1 v Three BridgesChatham Town 1-1 Three Bridges | Ryman League Division One South |
| 20 | Mon 6 Feb 2017 | 12-3 v SittingbourneChatham Town 2-3 Sittingbourne | Ryman League Division One South |
| 21 | Sat 11 Feb 2017 | 12-2 v Corinthian-CasualsCorinthian-Casuals 2-2 Chatham Town | Ryman League Division One South |
| 22 | Sat 18 Feb 2017 | 10-3 v Dorking WanderersChatham Town 0-3 Dorking Wanderers | Ryman League Division One South |
| 23 | Sat 25 Feb 2017 | 12-2 v Hastings UnitedHastings United 2-2 Chatham Town | Ryman League Division One South |
| 24 | Sat 4 Mar 2017 | 11-4 v HorshamChatham Town 1-4 Horsham | Ryman League Division One South |
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