| 1 | Sat 16 Aug 2014 | 21-4 v WareWare 4-1 Cray Wanderers | Ryman League Division One North |
| 2 | Sat 23 Aug 2014 | 152-3 v WroxhamCray Wanderers 2-3 Wroxham | Ryman League Division One North |
| 3 | Sat 30 Aug 2014 | 63-1 v MoleseyCray Wanderers 3-1 Molesey | FA Cup Preliminary Round |
| 4 | Tue 2 Sep 2014 | 61-2 v Maldon & TiptreeCray Wanderers 1-2 Maldon & Tiptree | Ryman League Division One North |
| 5 | Sat 13 Sep 2014 | 41-2 v Tooting & Mitcham UnitedCray Wanderers 1-2 Tooting & Mitcham United | FA Cup First Qualifying Round |
| 6 | Tue 16 Sep 2014 | 61-4 v CheshuntCray Wanderers 1-4 Cheshunt | Ryman League Division One North |
| 7 | Wed 24 Sep 2014 | 22-2 v RomfordRomford 2-2 Cray Wanderers | Ryman League Division One North |
| 8 | Sun 28 Sep 2014 | 22-0 v Burnham RamblersCray Wanderers 2-0 Burnham Ramblers | Ryman League Division One North |
| 9 | Tue 30 Sep 2014 | 41-4 v RedbridgeCray Wanderers 1-4 Redbridge | Ryman League Division One North |
| 10 | Tue 7 Oct 2014 | 42-4 v Maidstone UnitedMaidstone United 4-2 Cray Wanderers | Robert Dyas League Cup First Round |
| 11 | Sat 11 Oct 2014 | 161-1 v Soham Town RangersCray Wanderers 1-1 Soham Town Rangers | Ryman League Division One North |
| 12 | Sat 22 Nov 2014 | 41-2 v AFC SudburyAFC Sudbury 2-1 Cray Wanderers | Ryman League Division One North |
| 13 | Sat 29 Nov 2014 | 51-3 v WeymouthWeymouth 3-1 Cray Wanderers | FA Trophy Third Qualifying Round |
| 14 | Sun 14 Dec 2014 | 51-1 v WareCray Wanderers 1-1 Ware | Ryman League Division One North |
| 15 | Tue 16 Dec 2014 | 52-3 v Dereham TownCray Wanderers 2-3 Dereham Town | Ryman League Division One North |
| 16 | Sun 21 Dec 2014 | 52-2 v Harlow TownCray Wanderers 2-2 Harlow Town | Ryman League Division One North |
| 17 | Sat 27 Dec 2014 | 50-1 v Chatham TownChatham Town 1-0 Cray Wanderers | Ryman League Division One North |
| 18 | Tue 6 Jan 2015 | 60-3 v ThurrockCray Wanderers 0-3 Thurrock | Ryman League Division One North |
| 19 | Sat 10 Jan 2015 | 41-3 v Maldon & TiptreeMaldon & Tiptree 3-1 Cray Wanderers | Ryman League Division One North |
| 20 | Sat 7 Feb 2015 | 43-0 v Heybridge SwiftsCray Wanderers 3-0 Heybridge Swifts | Ryman League Division One North |
| 21 | Tue 10 Feb 2015 | 41-1 v Thamesmead TownCray Wanderers 1-1 Thamesmead Town | Ryman League Division One North |
| 22 | Tue 24 Feb 2015 | 40-3 v Brightlingsea RegentCray Wanderers 0-3 Brightlingsea Regent | Ryman League Division One North |
| 23 | Sat 28 Feb 2015 | 42-4 v Soham Town RangersSoham Town Rangers 4-2 Cray Wanderers | Ryman League Division One North |
| 24 | Sat 7 Mar 2015 | 61-1 v CheshuntCheshunt 1-1 Cray Wanderers | Ryman League Division One North |
| 25 | Tue 31 Mar 2015 | 153-1 v Great Wakering RoversCray Wanderers 3-1 Great Wakering Rovers | Ryman League Division One North |
| 26 | Sat 4 Apr 2015 | 62-0 v Harlow TownHarlow Town 0-2 Cray Wanderers | Ryman League Division One North |
| 27 | Mon 6 Apr 2015 | 63-0 v Chatham TownCray Wanderers 3-0 Chatham Town | Ryman League Division One North |
| 28 | Sat 11 Apr 2015 | 64-2 v Brightlingsea RegentBrightlingsea Regent 2-4 Cray Wanderers | Ryman League Division One North |
| 29 | Tue 14 Apr 2015 | 64-0 v Waltham AbbeyCray Wanderers 4-0 Waltham Abbey | Ryman League Division One North |
| 30 | Sat 25 Apr 2015 | 62-0 v Dereham TownDereham Town 0-2 Cray Wanderers | Ryman League Division One North |
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