| 1 | Sat 12 Aug | 10-1 v LewesLewes 1-0 Cray Wanderers | Isthmian League - Premier Division |
| 2 | Wed 16 Aug | 11-3 v HorshamCray Wanderers 1-3 Horsham | Isthmian League - Premier Division |
| 3 | Sat 19 Aug | 10-1 v Billericay TownCray Wanderers 0-1 Billericay Town | Isthmian League - Premier Division |
| 4 | Sat 26 Aug | 10-2 v Enfield TownEnfield Town 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 5 | Mon 28 Aug | 10-3 v Hastings UnitedHastings United 3-0 Cray Wanderers | Isthmian League - Premier Division |
| 6 | Sat 2 Sep | 1 5-1 v NewhavenCray Wanderers 5-1 Newhaven | Emirates FA Cup First Qualifying Round |
| 7 | Sat 9 Sep | 15-1 v Chatham TownChatham Town 1-5 Cray Wanderers | Isthmian League - Premier Division |
| 8 | Sun 17 Sep | 12-2 v RamsgateCray Wanderers 2-2 Ramsgate | Emirates FA Cup Second Qualifying Round |
| 9 | Wed 20 Sep | 12-3 v RamsgateRamsgate 3-2 Cray Wanderers | Emirates FA Cup Second Qualifying Round Replay |
| 10 | Sat 23 Sep | 12-1 v CheshuntCray Wanderers 2-1 Cheshunt | Isthmian League - Premier Division |
| 11 | Sat 30 Sep | 10-3 v KingstonianKingstonian 3-0 Cray Wanderers | Isthmian League - Premier Division |
| 12 | Tue 3 Oct | 13-0 v Concord RangersConcord Rangers 0-3 Cray Wanderers | Isthmian League - Premier Division |
| 13 | Sat 7 Oct | 11-0 v Needham MarketNeedham Market 0-1 Cray Wanderers | Isuzu FA Trophy Third Qualifying Round |
| 14 | Sun 15 Oct | 1 1-4 v HornchurchCray Wanderers 1-4 Hornchurch | Isthmian League - Premier Division |
| 15 | Sat 21 Oct | 11-1 v Potters Bar TownPotters Bar Town 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 16 | Tue 24 Oct | 11-2 v Canvey IslandCanvey Island 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 17 | Sat 28 Oct | 13-3 v Chesham UnitedCray Wanderers 3-3 Chesham United | Isuzu FA Trophy First Round |
| 18 | Tue 31 Oct | 10-5 v Ebbsfleet UnitedEbbsfleet United 5-0 Cray Wanderers | Kent Senior Cup Second Round |
| 19 | Sat 4 Nov | 13-1 v Wingate & FinchleyWingate & Finchley 1-3 Cray Wanderers | Isthmian League - Premier Division |
| 20 | Wed 8 Nov | 14-2 v Tooting & Mitcham UnitedCray Wanderers 4-2 Tooting & Mitcham United | London County Cup First Round |
| 21 | Sat 11 Nov | 1 1-0 v Carshalton AthleticCray Wanderers 1-0 Carshalton Athletic | Isthmian League - Premier Division |
| 22 | Sat 18 Nov | 11-4 v Weston-super-MareWeston-super-Mare 4-1 Cray Wanderers | Isuzu FA Trophy Second Round |
| 23 | Sat 25 Nov | 11-1 v Dulwich HamletCray Wanderers 1-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 24 | Wed 29 Nov | 12-2 v WhitehawkCray Wanderers 2-2 Whitehawk | Isthmian League - Premier Division |
| 25 | Sun 10 Dec | 13-3 v Haringey BoroughCray Wanderers 3-3 Haringey Borough | Isthmian League - Premier Division |
| 26 | Sat 16 Dec | 10-1 v Hashtag UnitedHashtag United 1-0 Cray Wanderers | Isthmian League - Premier Division |
| 27 | Tue 26 Dec | 10-0 v MargateCray Wanderers 0-0 Margate | Isthmian League - Premier Division |
| 28 | Fri 29 Dec | 12-0 v Enfield TownCray Wanderers 2-0 Enfield Town | Isthmian League - Premier Division |
| 29 | Mon 1 Jan | 10-0 v Hastings UnitedCray Wanderers 0-0 Hastings United | Isthmian League - Premier Division |
| 30 | Sat 6 Jan | 11-1 v LewesCray Wanderers 1-1 Lewes | Isthmian League - Premier Division |
| 31 | Tue 9 Jan | 1 1-2 v Bognor Regis TownBognor Regis Town 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 32 | Sat 13 Jan | 10-6 v Billericay TownBillericay Town 6-0 Cray Wanderers | Isthmian League - Premier Division |
| 33 | Wed 24 Jan | 13-0 v FisherCray Wanderers 3-0 Fisher | London County Cup Second Round |
| 34 | Sat 27 Jan | 11-0 v Wingate & FinchleyCray Wanderers 1-0 Wingate & Finchley | Isthmian League - Premier Division |
| 35 | Sat 3 Feb | 12-1 v Carshalton AthleticCarshalton Athletic 1-2 Cray Wanderers | Isthmian League - Premier Division |
| 36 | Tue 6 Feb | 12-2 v Folkestone InvictaFolkestone Invicta 2-2 Cray Wanderers | Isthmian League - Premier Division |
| 37 | Sun 11 Feb | 11-1 v Concord RangersCray Wanderers 1-1 Concord Rangers | Isthmian League - Premier Division |
| 38 | Sat 17 Feb | 11-0 v CheshuntCheshunt 0-1 Cray Wanderers | Isthmian League - Premier Division |
| 39 | Wed 21 Feb | 12-1 v Canvey IslandCray Wanderers 2-1 Canvey Island | Isthmian League - Premier Division |
| 40 | Sat 24 Feb | 11-0 v KingstonianCray Wanderers 1-0 Kingstonian | Isthmian League - Premier Division |
| 41 | Tue 27 Feb | 10-2 v WhitehawkWhitehawk 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 42 | Wed 13 Mar | 11-2 v Potters Bar TownCray Wanderers 1-2 Potters Bar Town | Isthmian League - Premier Division |
| 43 | Sat 16 Mar | 14-0 v Haringey BoroughHaringey Borough 0-4 Cray Wanderers | Isthmian League - Premier Division |
| 44 | Sun 24 Mar | 10-1 v Folkestone InvictaCray Wanderers 0-1 Folkestone Invicta | Isthmian League - Premier Division |
| 45 | Fri 29 Mar | 12-2 v Chatham TownCray Wanderers 2-2 Chatham Town | Isthmian League - Premier Division |
| 46 | Mon 1 Apr | 11-1 v MargateMargate 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 47 | Fri 5 Apr | 11-3 v Hashtag UnitedCray Wanderers 1-3 Hashtag United | Isthmian League - Premier Division |
| 48 | Tue 9 Apr | 10-2 v HornchurchHornchurch 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 49 | Sat 13 Apr | 10-2 v HorshamHorsham 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 50 | Tue 16 Apr | 11-2 v DartfordCray Wanderers 1-2 Dartford | London County Cup Quarter Final |
| 51 | Sat 20 Apr | 11-5 v Bognor Regis TownCray Wanderers 1-5 Bognor Regis Town | Isthmian League - Premier Division |
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