| 1 | Sat 12 Aug | 190-1 v LewesLewes 1-0 Cray Wanderers | Isthmian League - Premier Division |
| 2 | Wed 16 Aug | 191-3 v HorshamCray Wanderers 1-3 Horsham | Isthmian League - Premier Division |
| 3 | Sat 26 Aug | 190-2 v Enfield TownEnfield Town 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 4 | Sat 2 Sep | 4 5-1 v NewhavenCray Wanderers 5-1 Newhaven | Emirates FA Cup First Qualifying Round |
| 5 | Sat 9 Sep | 4 5-1 v Chatham TownChatham Town 1-5 Cray Wanderers | Isthmian League - Premier Division |
| 6 | Sun 17 Sep | 4 2-2 v RamsgateCray Wanderers 2-2 Ramsgate | Emirates FA Cup Second Qualifying Round |
| 7 | Wed 20 Sep | 4 2-3 v RamsgateRamsgate 3-2 Cray Wanderers | Emirates FA Cup Second Qualifying Round Replay |
| 8 | Sat 23 Sep | 42-1 v CheshuntCray Wanderers 2-1 Cheshunt | Isthmian League - Premier Division |
| 9 | Sat 30 Sep | 40-3 v KingstonianKingstonian 3-0 Cray Wanderers | Isthmian League - Premier Division |
| 10 | Tue 3 Oct | 73-0 v Concord RangersConcord Rangers 0-3 Cray Wanderers | Isthmian League - Premier Division |
| 11 | Sat 7 Oct | 41-0 v Needham MarketNeedham Market 0-1 Cray Wanderers | Isuzu FA Trophy Third Qualifying Round |
| 12 | Sun 15 Oct | 41-4 v HornchurchCray Wanderers 1-4 Hornchurch | Isthmian League - Premier Division |
| 13 | Sat 21 Oct | 41-1 v Potters Bar TownPotters Bar Town 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 14 | Tue 24 Oct | 41-2 v Canvey IslandCanvey Island 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 15 | Sat 28 Oct | 4 3-3 v Chesham UnitedCray Wanderers 3-3 Chesham United | Isuzu FA Trophy First Round |
| 16 | Sat 4 Nov | 4 3-1 v Wingate & FinchleyWingate & Finchley 1-3 Cray Wanderers | Isthmian League - Premier Division |
| 17 | Sat 11 Nov | 4 1-0 v Carshalton AthleticCray Wanderers 1-0 Carshalton Athletic | Isthmian League - Premier Division |
| 18 | Sat 18 Nov | 41-4 v Weston-super-MareWeston-super-Mare 4-1 Cray Wanderers | Isuzu FA Trophy Second Round |
| 19 | Sat 25 Nov | 41-1 v Dulwich HamletCray Wanderers 1-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 20 | Wed 29 Nov | 42-2 v WhitehawkCray Wanderers 2-2 Whitehawk | Isthmian League - Premier Division |
| 21 | Sun 10 Dec | 43-3 v Haringey BoroughCray Wanderers 3-3 Haringey Borough | Isthmian League - Premier Division |
| 22 | Sat 16 Dec | 40-1 v Hashtag UnitedHashtag United 1-0 Cray Wanderers | Isthmian League - Premier Division |
| 23 | Tue 26 Dec | 4 0-0 v MargateCray Wanderers 0-0 Margate | Isthmian League - Premier Division |
| 24 | Fri 29 Dec | 42-0 v Enfield TownCray Wanderers 2-0 Enfield Town | Isthmian League - Premier Division |
| 25 | Mon 1 Jan | 40-0 v Hastings UnitedCray Wanderers 0-0 Hastings United | Isthmian League - Premier Division |
| 26 | Sat 6 Jan | 4 1-1 v LewesCray Wanderers 1-1 Lewes | Isthmian League - Premier Division |
| 27 | Tue 9 Jan | 41-2 v Bognor Regis TownBognor Regis Town 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 28 | Sat 13 Jan | 4 0-6 v Billericay TownBillericay Town 6-0 Cray Wanderers | Isthmian League - Premier Division |
| 29 | Sat 27 Jan | 41-0 v Wingate & FinchleyCray Wanderers 1-0 Wingate & Finchley | Isthmian League - Premier Division |
| 30 | Sat 3 Feb | 42-1 v Carshalton AthleticCarshalton Athletic 1-2 Cray Wanderers | Isthmian League - Premier Division |
| 31 | Tue 6 Feb | 19 2-2 v Folkestone InvictaFolkestone Invicta 2-2 Cray Wanderers | Isthmian League - Premier Division |
| 32 | Sun 11 Feb | 41-1 v Concord RangersCray Wanderers 1-1 Concord Rangers | Isthmian League - Premier Division |
| 33 | Sat 17 Feb | 41-0 v CheshuntCheshunt 0-1 Cray Wanderers | Isthmian League - Premier Division |
| 34 | Wed 21 Feb | 42-1 v Canvey IslandCray Wanderers 2-1 Canvey Island | Isthmian League - Premier Division |
| 35 | Sat 24 Feb | 41-0 v KingstonianCray Wanderers 1-0 Kingstonian | Isthmian League - Premier Division |
| 36 | Tue 27 Feb | 4 0-2 v WhitehawkWhitehawk 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 37 | Sat 16 Mar | 44-0 v Haringey BoroughHaringey Borough 0-4 Cray Wanderers | Isthmian League - Premier Division |
| 38 | Sun 24 Mar | 40-1 v Folkestone InvictaCray Wanderers 0-1 Folkestone Invicta | Isthmian League - Premier Division |
| 39 | Fri 29 Mar | 42-2 v Chatham TownCray Wanderers 2-2 Chatham Town | Isthmian League - Premier Division |
| 40 | Mon 1 Apr | 41-1 v MargateMargate 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 41 | Fri 5 Apr | 41-3 v Hashtag UnitedCray Wanderers 1-3 Hashtag United | Isthmian League - Premier Division |
| 42 | Tue 9 Apr | 40-2 v HornchurchHornchurch 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 43 | Sat 13 Apr | 40-2 v HorshamHorsham 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 44 | Sat 27 Apr | 46-2 v Dulwich HamletDulwich Hamlet 2-6 Cray Wanderers | Isthmian League - Premier Division |
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