| 1 | Sat 11 Jan 2014 | 10-1 v Enfield TownEnfield Town 1-0 Cray Wanderers | Ryman League Premier Division |
| 2 | Tue 21 Jan 2014 | 11-2 v Bognor Regis TownCray Wanderers 1-2 Bognor Regis Town | Ryman League Premier Division |
| 3 | Tue 11 Feb 2014 | 10-3 v Maidstone UnitedMaidstone United 3-0 Cray Wanderers | Ryman League Premier Division |
| 4 | Sun 23 Feb 2014 | 11-5 v LewesCray Wanderers 1-5 Lewes | Ryman League Premier Division |
| 5 | Tue 25 Feb 2014 | 11-1 v Hampton & Richmond BoroughCray Wanderers 1-1 Hampton & Richmond Borough | Ryman League Premier Division |
| 6 | Sat 1 Mar 2014 | 11-7 v Metropolitan PoliceMetropolitan Police 7-1 Cray Wanderers | Ryman League Premier Division |
| 7 | Sat 8 Mar 2014 | 10-4 v Lowestoft TownCray Wanderers 0-4 Lowestoft Town | Ryman League Premier Division |
| 8 | Sat 15 Mar 2014 | 10-2 v HendonHendon 2-0 Cray Wanderers | Ryman League Premier Division |
| 9 | Tue 18 Mar 2014 | 12-1 v AFC HornchurchAFC Hornchurch 1-2 Cray Wanderers | Ryman League Premier Division |
| 10 | Thu 20 Mar 2014 | 10-3 v Grays AthleticGrays Athletic 3-0 Cray Wanderers | Ryman League Premier Division |
| 11 | Sun 23 Mar 2014 | 12-2 v Wingate & FinchleyCray Wanderers 2-2 Wingate & Finchley | Ryman League Premier Division |
| 12 | Tue 25 Mar 2014 | 13-2 v Grays AthleticCray Wanderers 3-2 Grays Athletic | Ryman League Premier Division |
| 13 | Sat 29 Mar 2014 | 12-1 v Billericay TownBillericay Town 1-2 Cray Wanderers | Ryman League Premier Division |
| 14 | Sat 5 Apr 2014 | 10-4 v KingstonianCray Wanderers 0-4 Kingstonian | Ryman League Premier Division |
| 15 | Sat 12 Apr 2014 | 10-1 v Bury TownBury Town 1-0 Cray Wanderers | Ryman League Premier Division |
| 16 | Tue 15 Apr 2014 | 11-3 v East Thurrock UnitedCray Wanderers 1-3 East Thurrock United | Ryman League Premier Division |
| 17 | Sat 19 Apr 2014 | 10-1 v Harrow BoroughCray Wanderers 0-1 Harrow Borough | Ryman League Premier Division |
| 18 | Mon 21 Apr 2014 | 10-5 v MargateMargate 5-0 Cray Wanderers | Ryman League Premier Division |
| 19 | Sat 26 Apr 2014 | 11-2 v Enfield TownCray Wanderers 1-2 Enfield Town | Ryman League Premier Division |
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