| 1 | Sat 13 Jul | 10-4 v SheffieldCray Wanderers 0-4 Sheffield | Friendly |
| 2 | Sat 10 Aug | 12-0 v Hashtag UnitedHashtag United 0-2 Cray Wanderers | Isthmian League - Premier Division |
| 3 | Tue 13 Aug | 10-2 v Cray Valley PMCray Wanderers 0-2 Cray Valley PM | Isthmian League - Premier Division |
| 4 | Sat 17 Aug | 11-3 v HendonHendon 3-1 Cray Wanderers | Isthmian League - Premier Division |
| 5 | Sat 24 Aug | 11-3 v LewesCray Wanderers 1-3 Lewes | Isthmian League - Premier Division |
| 6 | Mon 26 Aug | 11-2 v Dulwich HamletDulwich Hamlet 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 7 | Sat 31 Aug | 11-1 v Larkfield & New HytheLarkfield & New Hythe 1-1 Cray Wanderers | Emirates FA Cup First Qualifying Round |
| 8 | Tue 3 Sep | 18-0 v Larkfield & New HytheCray Wanderers 8-0 Larkfield & New Hythe | Emirates FA Cup First Qualifying Round Replay |
| 9 | Sat 7 Sep | 10-0 v HorshamCray Wanderers 0-0 Horsham | Isthmian League - Premier Division |
| 10 | Sat 14 Sep | 11-1 v Wingate & FinchleyCray Wanderers 1-1 Wingate & Finchley | Emirates FA Cup Second Qualifying Round |
| 11 | Tue 17 Sep | 11-0 v Wingate & FinchleyWingate & Finchley 0-1 Cray Wanderers | Emirates FA Cup Second Qualifying Round Replay |
| 12 | Sat 21 Sep | 11-3 v Bognor Regis TownBognor Regis Town 3-1 Cray Wanderers | Isthmian League - Premier Division |
| 13 | Sat 28 Sep | 13-0 v Hastings UnitedCray Wanderers 3-0 Hastings United | Emirates FA Cup Third Qualifying Round |
| 14 | Sat 5 Oct | 11-1 v Brentwood TownBrentwood Town 1-1 Cray Wanderers | Isuzu FA Trophy Third Qualifying Round |
| 15 | Sat 12 Oct | 10-1 v Tonbridge AngelsCray Wanderers 0-1 Tonbridge Angels | Emirates FA Cup Fourth Qualifying Round |
| 16 | Tue 15 Oct | 11-4 v Chatham TownCray Wanderers 1-4 Chatham Town | Isthmian League - Premier Division |
| 17 | Sat 19 Oct | 10-0 v Hastings UnitedCray Wanderers 0-0 Hastings United | Isthmian League - Premier Division |
| 18 | Tue 22 Oct | 10-0 v WhitehawkCray Wanderers 0-0 Whitehawk | Isthmian League - Premier Division |
| 19 | Sat 26 Oct | 11-0 v CheshuntCheshunt 0-1 Cray Wanderers | Isthmian League - Premier Division |
| 20 | Sat 2 Nov | 13-0 v Hashtag UnitedCray Wanderers 3-0 Hashtag United | Isthmian League - Premier Division |
| 21 | Tue 5 Nov | 11-2 v Cray Valley PMCray Valley PM 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 22 | Sat 9 Nov | 10-1 v Folkestone InvictaFolkestone Invicta 1-0 Cray Wanderers | Isthmian League - Premier Division |
| 23 | Sat 16 Nov | 14-0 v Potters Bar TownPotters Bar Town 0-4 Cray Wanderers | Isthmian League - Premier Division |
| 24 | Sat 23 Nov | 10-2 v Canvey IslandCanvey Island 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 25 | Sat 30 Nov | 11-1 v Carshalton AthleticCray Wanderers 1-1 Carshalton Athletic | Isthmian League - Premier Division |
| 26 | Sat 7 Dec | 11-0 v Bowers & PitseaBowers & Pitsea 0-1 Cray Wanderers | Isthmian League - Premier Division |
| 27 | Tue 10 Dec | 11-0 v Chichester CityCray Wanderers 1-0 Chichester City | Isthmian League - Premier Division |
| 28 | Sat 14 Dec | 11-0 v Dover AthleticDover Athletic 0-1 Cray Wanderers | Isthmian League - Premier Division |
| 29 | Sat 21 Dec | 11-1 v Billericay TownCray Wanderers 1-1 Billericay Town | Isthmian League - Premier Division |
| 30 | Thu 26 Dec | 11-2 v DartfordDartford 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 31 | Sat 28 Dec | 11-0 v HendonCray Wanderers 1-0 Hendon | Isthmian League - Premier Division |
| 32 | Wed 1 Jan | 11-0 v Dulwich HamletCray Wanderers 1-0 Dulwich Hamlet | Isthmian League - Premier Division |
| 33 | Sat 11 Jan | 11-0 v Potters Bar TownCray Wanderers 1-0 Potters Bar Town | Isthmian League - Premier Division |
| 34 | Sat 18 Jan | 12-1 v Hastings UnitedHastings United 1-2 Cray Wanderers | Isthmian League - Premier Division |
| 35 | Sat 25 Jan | 1 0-2 v WhitehawkWhitehawk 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 36 | Tue 28 Jan | 10-1 v Wingate & FinchleyWingate & Finchley 1-0 Cray Wanderers | Isthmian League - Premier Division |
| 37 | Sat 1 Feb | 11-1 v Bognor Regis TownCray Wanderers 1-1 Bognor Regis Town | Isthmian League - Premier Division |
| 38 | Sat 8 Feb | 14-1 v Chatham TownChatham Town 1-4 Cray Wanderers | Isthmian League - Premier Division |
| 39 | Sat 15 Feb | 12-1 v CheshuntCray Wanderers 2-1 Cheshunt | Isthmian League - Premier Division |
| 40 | Sat 22 Feb | 13-2 v Folkestone InvictaCray Wanderers 3-2 Folkestone Invicta | Isthmian League - Premier Division |
| 41 | Sat 1 Mar | 11-2 v Chichester CityChichester City 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 42 | Sat 8 Mar | 13-1 v Canvey IslandCray Wanderers 3-1 Canvey Island | Isthmian League - Premier Division |
| 43 | Sat 15 Mar | 11-2 v Carshalton AthleticCarshalton Athletic 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 44 | Sat 22 Mar | 14-0 v Bowers & PitseaCray Wanderers 4-0 Bowers & Pitsea | Isthmian League - Premier Division |
| 45 | Sat 29 Mar | 11-2 v Dover AthleticCray Wanderers 1-2 Dover Athletic | Isthmian League - Premier Division |
| 46 | Sat 5 Apr | 12-0 v Billericay TownBillericay Town 0-2 Cray Wanderers | Isthmian League - Premier Division |
| 47 | Fri 18 Apr | 10-3 v HorshamHorsham 3-0 Cray Wanderers | Isthmian League - Premier Division |
| 48 | Mon 21 Apr | 1 2-2 v DartfordCray Wanderers 2-2 Dartford | Isthmian League - Premier Division |
| 49 | Sat 26 Apr | 13-4 v LewesLewes 4-3 Cray Wanderers | Isthmian League - Premier Division |
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