| 1 | Sat 23 Jul 2016 | 51-0 v LordswoodLordswood 0-1 Cray Wanderers | Friendly |
| 2 | Sat 13 Aug 2016 | 53-3 v SittingbourneCray Wanderers 3-3 Sittingbourne | Ryman League Division One South |
| 3 | Sat 20 Aug 2016 | 54-0 v Badshot LeaBadshot Lea 0-4 Cray Wanderers | Emirates FA Cup Preliminary Round |
| 4 | Sat 27 Aug 2016 | 51-0 v Faversham TownCray Wanderers 1-0 Faversham Town | Ryman League Division One South |
| 5 | Mon 29 Aug 2016 | 53-1 v Chatham TownChatham Town 1-3 Cray Wanderers | Ryman League Division One South |
| 6 | Sat 3 Sep 2016 | 50-1 v Faversham TownFaversham Town 1-0 Cray Wanderers | Emirates FA Cup First Qualifying Round |
| 7 | Tue 6 Sep 2016 | 52-2 v RamsgateRamsgate 2-2 Cray Wanderers | Ryman League Division One South |
| 8 | Sat 10 Sep 2016 | 51-2 v Dorking WanderersDorking Wanderers 2-1 Cray Wanderers | Ryman League Division One South |
| 9 | Sat 17 Sep 2016 | 53-2 v Three BridgesCray Wanderers 3-2 Three Bridges | Ryman League Division One South |
| 10 | Wed 21 Sep 2016 | 50-1 v Hythe TownCray Wanderers 0-1 Hythe Town | Ryman League Division One South |
| 11 | Sat 24 Sep 2016 | 51-0 v Godalming TownGodalming Town 0-1 Cray Wanderers | Ryman League Division One South |
| 12 | Sat 1 Oct 2016 | 53-0 v MoleseyCray Wanderers 3-0 Molesey | Ryman League Division One South |
| 13 | Sun 9 Oct 2016 | 53-3 v Carshalton AthleticCray Wanderers 3-3 Carshalton Athletic | FA Trophy Preliminary Round |
| 14 | Sat 15 Oct 2016 | 54-1 v Carshalton AthleticCray Wanderers 4-1 Carshalton Athletic | Ryman League Division One South |
| 15 | Wed 19 Oct 2016 | 51-0 v GuernseyCray Wanderers 1-0 Guernsey | Ryman League Division One South |
| 16 | Sat 22 Oct 2016 | 52-5 v LewesLewes 5-2 Cray Wanderers | Ryman League Division One South |
| 17 | Wed 26 Oct 2016 | 53-0 v Carshalton AthleticCray Wanderers 3-0 Carshalton Athletic | FA Trophy Preliminary Round |
| 18 | Sat 29 Oct 2016 | 54-0 v MarlowCray Wanderers 4-0 Marlow | FA Trophy First Qualifying Round |
| 19 | Sat 5 Nov 2016 | 50-4 v Tooting & Mitcham UnitedTooting & Mitcham United 4-0 Cray Wanderers | Ryman League Division One South |
| 20 | Sun 13 Nov 2016 | 51-2 v WorthingCray Wanderers 1-2 Worthing | FA Trophy Second Qualifying Round |
| 21 | Sun 4 Dec 2016 | 165-1 v Godalming TownCray Wanderers 5-1 Godalming Town | Ryman League Division One South |
| 22 | Sat 17 Dec 2016 | 52-4 v East Grinstead TownCray Wanderers 2-4 East Grinstead Town | Ryman League Division One South |
| 23 | Mon 26 Dec 2016 | 51-3 v Greenwich BoroughGreenwich Borough 3-1 Cray Wanderers | Ryman League Division One South |
| 24 | Sat 31 Dec 2016 | 52-2 v RamsgateCray Wanderers 2-2 Ramsgate | Ryman League Division One South |
| 25 | Mon 2 Jan 2017 | 53-0 v Chatham TownCray Wanderers 3-0 Chatham Town | Ryman League Division One South |
| 26 | Sat 7 Jan 2017 | 52-1 v Hastings UnitedHastings United 1-2 Cray Wanderers | Ryman League Division One South |
| 27 | Sat 14 Jan 2017 | 51-1 v Corinthian-CasualsCorinthian-Casuals 1-1 Cray Wanderers | Ryman League Division One South |
| 28 | Wed 1 Feb 2017 | 51-0 v Herne BayHerne Bay 0-1 Cray Wanderers | Ryman League Division One South |
| 29 | Sat 18 Feb 2017 | 51-2 v Carshalton AthleticCarshalton Athletic 2-1 Cray Wanderers | Ryman League Division One South |
| 30 | Wed 22 Feb 2017 | 51-4 v Tooting & Mitcham UnitedCray Wanderers 1-4 Tooting & Mitcham United | Ryman League Division One South |
| 31 | Wed 1 Mar 2017 | 53-4 v Corinthian-CasualsCray Wanderers 3-4 Corinthian-Casuals | Ryman League Division One South |
| 32 | Sat 18 Mar 2017 | 50-3 v South ParkCray Wanderers 0-3 South Park | Ryman League Division One South |
| 33 | Sat 25 Mar 2017 | 51-0 v WhyteleafeWhyteleafe 0-1 Cray Wanderers | Ryman League Division One South |
| 34 | Sat 1 Apr 2017 | 50-2 v Dorking WanderersCray Wanderers 0-2 Dorking Wanderers | Ryman League Division One South |
| 35 | Sun 9 Apr 2017 | 51-4 v Hastings UnitedCray Wanderers 1-4 Hastings United | Ryman League Division One South |
| 36 | Mon 17 Apr 2017 | 50-0 v Greenwich BoroughCray Wanderers 0-0 Greenwich Borough | Ryman League Division One South |
| 37 | Sat 22 Apr 2017 | 52-2 v Faversham TownFaversham Town 2-2 Cray Wanderers | Ryman League Division One South |
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