| 1 | Sat 12 Aug | 50-1 v LewesLewes 1-0 Cray Wanderers | Isthmian League - Premier Division |
| 2 | Wed 16 Aug | 51-3 v HorshamCray Wanderers 1-3 Horsham | Isthmian League - Premier Division |
| 3 | Sat 19 Aug | 5 0-1 v Billericay TownCray Wanderers 0-1 Billericay Town | Isthmian League - Premier Division |
| 4 | Sat 26 Aug | 50-2 v Enfield TownEnfield Town 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 5 | Mon 28 Aug | 5 0-3 v Hastings UnitedHastings United 3-0 Cray Wanderers | Isthmian League - Premier Division |
| 6 | Sat 2 Sep | 5 5-1 v NewhavenCray Wanderers 5-1 Newhaven | Emirates FA Cup First Qualifying Round |
| 7 | Sat 9 Sep | 55-1 v Chatham TownChatham Town 1-5 Cray Wanderers | Isthmian League - Premier Division |
| 8 | Sun 17 Sep | 52-2 v RamsgateCray Wanderers 2-2 Ramsgate | Emirates FA Cup Second Qualifying Round |
| 9 | Wed 20 Sep | 5 2-3 v RamsgateRamsgate 3-2 Cray Wanderers | Emirates FA Cup Second Qualifying Round Replay |
| 10 | Sat 23 Sep | 52-1 v CheshuntCray Wanderers 2-1 Cheshunt | Isthmian League - Premier Division |
| 11 | Tue 3 Oct | 43-0 v Concord RangersConcord Rangers 0-3 Cray Wanderers | Isthmian League - Premier Division |
| 12 | Sat 7 Oct | 51-0 v Needham MarketNeedham Market 0-1 Cray Wanderers | Isuzu FA Trophy Third Qualifying Round |
| 13 | Sun 15 Oct | 51-4 v HornchurchCray Wanderers 1-4 Hornchurch | Isthmian League - Premier Division |
| 14 | Sat 21 Oct | 51-1 v Potters Bar TownPotters Bar Town 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 15 | Tue 24 Oct | 5 1-2 v Canvey IslandCanvey Island 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 16 | Sat 28 Oct | 53-3 v Chesham UnitedCray Wanderers 3-3 Chesham United | Isuzu FA Trophy First Round |
| 17 | Sat 18 Nov | 51-4 v Weston-super-MareWeston-super-Mare 4-1 Cray Wanderers | Isuzu FA Trophy Second Round |
| 18 | Wed 29 Nov | 52-2 v WhitehawkCray Wanderers 2-2 Whitehawk | Isthmian League - Premier Division |
| 19 | Tue 26 Dec | 5 0-0 v MargateCray Wanderers 0-0 Margate | Isthmian League - Premier Division |
| 20 | Fri 29 Dec | 52-0 v Enfield TownCray Wanderers 2-0 Enfield Town | Isthmian League - Premier Division |
| 21 | Mon 1 Jan | 50-0 v Hastings UnitedCray Wanderers 0-0 Hastings United | Isthmian League - Premier Division |
| 22 | Sat 6 Jan | 51-1 v LewesCray Wanderers 1-1 Lewes | Isthmian League - Premier Division |
| 23 | Tue 9 Jan | 5 1-2 v Bognor Regis TownBognor Regis Town 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 24 | Sat 13 Jan | 50-6 v Billericay TownBillericay Town 6-0 Cray Wanderers | Isthmian League - Premier Division |
| 25 | Sun 24 Mar | 60-1 v Folkestone InvictaCray Wanderers 0-1 Folkestone Invicta | Isthmian League - Premier Division |
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