| 1 | Sat 12 Aug | 200-1 v LewesLewes 1-0 Cray Wanderers | Isthmian League - Premier Division |
| 2 | Wed 16 Aug | 201-3 v HorshamCray Wanderers 1-3 Horsham | Isthmian League - Premier Division |
| 3 | Sat 26 Aug | 200-2 v Enfield TownEnfield Town 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 4 | Mon 28 Aug | 20 0-3 v Hastings UnitedHastings United 3-0 Cray Wanderers | Isthmian League - Premier Division |
| 5 | Sat 2 Sep | 205-1 v NewhavenCray Wanderers 5-1 Newhaven | Emirates FA Cup First Qualifying Round |
| 6 | Sun 17 Sep | 202-2 v RamsgateCray Wanderers 2-2 Ramsgate | Emirates FA Cup Second Qualifying Round |
| 7 | Wed 20 Sep | 20 2-3 v RamsgateRamsgate 3-2 Cray Wanderers | Emirates FA Cup Second Qualifying Round Replay |
| 8 | Sat 23 Sep | 202-1 v CheshuntCray Wanderers 2-1 Cheshunt | Isthmian League - Premier Division |
| 9 | Tue 26 Sep | 203-2 v Phoenix SportsPhoenix Sports 2-3 Cray Wanderers | Kent Senior Cup First Round |
| 10 | Sat 30 Sep | 200-3 v KingstonianKingstonian 3-0 Cray Wanderers | Isthmian League - Premier Division |
| 11 | Tue 3 Oct | 163-0 v Concord RangersConcord Rangers 0-3 Cray Wanderers | Isthmian League - Premier Division |
| 12 | Sat 7 Oct | 201-0 v Needham MarketNeedham Market 0-1 Cray Wanderers | Isuzu FA Trophy Third Qualifying Round |
| 13 | Sun 15 Oct | 201-4 v HornchurchCray Wanderers 1-4 Hornchurch | Isthmian League - Premier Division |
| 14 | Sat 21 Oct | 201-1 v Potters Bar TownPotters Bar Town 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 15 | Tue 24 Oct | 201-2 v Canvey IslandCanvey Island 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 16 | Sat 28 Oct | 203-3 v Chesham UnitedCray Wanderers 3-3 Chesham United | Isuzu FA Trophy First Round |
| 17 | Tue 31 Oct | 200-5 v Ebbsfleet UnitedEbbsfleet United 5-0 Cray Wanderers | Kent Senior Cup Second Round |
| 18 | Sat 4 Nov | 203-1 v Wingate & FinchleyWingate & Finchley 1-3 Cray Wanderers | Isthmian League - Premier Division |
| 19 | Wed 8 Nov | 204-2 v Tooting & Mitcham UnitedCray Wanderers 4-2 Tooting & Mitcham United | London County Cup First Round |
| 20 | Sat 11 Nov | 201-0 v Carshalton AthleticCray Wanderers 1-0 Carshalton Athletic | Isthmian League - Premier Division |
| 21 | Sat 18 Nov | 201-4 v Weston-super-MareWeston-super-Mare 4-1 Cray Wanderers | Isuzu FA Trophy Second Round |
| 22 | Sat 25 Nov | 201-1 v Dulwich HamletCray Wanderers 1-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 23 | Wed 29 Nov | 202-2 v WhitehawkCray Wanderers 2-2 Whitehawk | Isthmian League - Premier Division |
| 24 | Sat 16 Dec | 200-1 v Hashtag UnitedHashtag United 1-0 Cray Wanderers | Isthmian League - Premier Division |
| 25 | Tue 26 Dec | 200-0 v MargateCray Wanderers 0-0 Margate | Isthmian League - Premier Division |
| 26 | Sat 6 Jan | 201-1 v LewesCray Wanderers 1-1 Lewes | Isthmian League - Premier Division |
| 27 | Tue 9 Jan | 201-2 v Bognor Regis TownBognor Regis Town 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 28 | Sat 13 Jan | 20 0-6 v Billericay TownBillericay Town 6-0 Cray Wanderers | Isthmian League - Premier Division |
| 29 | Wed 24 Jan | 203-0 v FisherCray Wanderers 3-0 Fisher | London County Cup Second Round |
| 30 | Sat 27 Jan | 201-0 v Wingate & FinchleyCray Wanderers 1-0 Wingate & Finchley | Isthmian League - Premier Division |
| 31 | Sat 3 Feb | 202-1 v Carshalton AthleticCarshalton Athletic 1-2 Cray Wanderers | Isthmian League - Premier Division |
| 32 | Tue 6 Feb | 202-2 v Folkestone InvictaFolkestone Invicta 2-2 Cray Wanderers | Isthmian League - Premier Division |
| 33 | Sun 11 Feb | 20 1-1 v Concord RangersCray Wanderers 1-1 Concord Rangers | Isthmian League - Premier Division |
| 34 | Sat 17 Feb | 201-0 v CheshuntCheshunt 0-1 Cray Wanderers | Isthmian League - Premier Division |
| 35 | Wed 21 Feb | 202-1 v Canvey IslandCray Wanderers 2-1 Canvey Island | Isthmian League - Premier Division |
| 36 | Sat 24 Feb | 20 1-0 v KingstonianCray Wanderers 1-0 Kingstonian | Isthmian League - Premier Division |
| 37 | Tue 27 Feb | 200-2 v WhitehawkWhitehawk 2-0 Cray Wanderers | Isthmian League - Premier Division |
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