| 1 | Sat 10 Aug | 52-0 v Hashtag UnitedHashtag United 0-2 Cray Wanderers | Isthmian League - Premier Division |
| 2 | Tue 13 Aug | 5 0-2 v Cray Valley PMCray Wanderers 0-2 Cray Valley PM | Isthmian League - Premier Division |
| 3 | Sat 17 Aug | 51-3 v HendonHendon 3-1 Cray Wanderers | Isthmian League - Premier Division |
| 4 | Sat 24 Aug | 5 1-3 v LewesCray Wanderers 1-3 Lewes | Isthmian League - Premier Division |
| 5 | Mon 26 Aug | 51-2 v Dulwich HamletDulwich Hamlet 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 6 | Sat 31 Aug | 51-1 v Larkfield & New HytheLarkfield & New Hythe 1-1 Cray Wanderers | Emirates FA Cup First Qualifying Round |
| 7 | Tue 3 Sep | 58-0 v Larkfield & New HytheCray Wanderers 8-0 Larkfield & New Hythe | Emirates FA Cup First Qualifying Round Replay |
| 8 | Sat 14 Sep | 51-1 v Wingate & FinchleyCray Wanderers 1-1 Wingate & Finchley | Emirates FA Cup Second Qualifying Round |
| 9 | Sat 21 Sep | 5 1-3 v Bognor Regis TownBognor Regis Town 3-1 Cray Wanderers | Isthmian League - Premier Division |
| 10 | Tue 24 Sep | 52-1 v Chatham TownChatham Town 1-2 Cray Wanderers | Kent Senior Cup First Round |
| 11 | Sat 12 Oct | 50-1 v Tonbridge AngelsCray Wanderers 0-1 Tonbridge Angels | Emirates FA Cup Fourth Qualifying Round |
| 12 | Tue 15 Oct | 51-4 v Chatham TownCray Wanderers 1-4 Chatham Town | Isthmian League - Premier Division |
| 13 | Sat 19 Oct | 5 0-0 v Hastings UnitedCray Wanderers 0-0 Hastings United | Isthmian League - Premier Division |
| 14 | Tue 22 Oct | 50-0 v WhitehawkCray Wanderers 0-0 Whitehawk | Isthmian League - Premier Division |
| 15 | Sat 26 Oct | 51-0 v CheshuntCheshunt 0-1 Cray Wanderers | Isthmian League - Premier Division |
| 16 | Sat 2 Nov | 53-0 v Hashtag UnitedCray Wanderers 3-0 Hashtag United | Isthmian League - Premier Division |
| 17 | Tue 5 Nov | 51-2 v Cray Valley PMCray Valley PM 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 18 | Sat 9 Nov | 5 0-1 v Folkestone InvictaFolkestone Invicta 1-0 Cray Wanderers | Isthmian League - Premier Division |
| 19 | Tue 19 Nov | 54-7 v Erith TownCray Wanderers 4-7 Erith Town | London Senior Cup Second Round |
| 20 | Sat 7 Dec | 51-0 v Bowers & PitseaBowers & Pitsea 0-1 Cray Wanderers | Isthmian League - Premier Division |
| 21 | Tue 10 Dec | 5 1-0 v Chichester CityCray Wanderers 1-0 Chichester City | Isthmian League - Premier Division |
| 22 | Sat 14 Dec | 51-0 v Dover AthleticDover Athletic 0-1 Cray Wanderers | Isthmian League - Premier Division |
| 23 | Wed 1 Jan | 51-0 v Dulwich HamletCray Wanderers 1-0 Dulwich Hamlet | Isthmian League - Premier Division |
| 24 | Sat 11 Jan | 51-0 v Potters Bar TownCray Wanderers 1-0 Potters Bar Town | Isthmian League - Premier Division |
| 25 | Sat 18 Jan | 52-1 v Hastings UnitedHastings United 1-2 Cray Wanderers | Isthmian League - Premier Division |
| 26 | Sat 25 Jan | 50-2 v WhitehawkWhitehawk 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 27 | Sat 1 Feb | 51-1 v Bognor Regis TownCray Wanderers 1-1 Bognor Regis Town | Isthmian League - Premier Division |
| 28 | Sat 8 Feb | 54-1 v Chatham TownChatham Town 1-4 Cray Wanderers | Isthmian League - Premier Division |
| 29 | Sat 15 Feb | 52-1 v CheshuntCray Wanderers 2-1 Cheshunt | Isthmian League - Premier Division |
| 30 | Sat 22 Feb | 53-2 v Folkestone InvictaCray Wanderers 3-2 Folkestone Invicta | Isthmian League - Premier Division |
| 31 | Sat 1 Mar | 51-2 v Chichester CityChichester City 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 32 | Sat 15 Mar | 51-2 v Carshalton AthleticCarshalton Athletic 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 33 | Sat 22 Mar | 64-0 v Bowers & PitseaCray Wanderers 4-0 Bowers & Pitsea | Isthmian League - Premier Division |
| 34 | Sat 29 Mar | 51-2 v Dover AthleticCray Wanderers 1-2 Dover Athletic | Isthmian League - Premier Division |
| 35 | Sat 5 Apr | 52-0 v Billericay TownBillericay Town 0-2 Cray Wanderers | Isthmian League - Premier Division |
| 36 | Fri 18 Apr | 50-3 v HorshamHorsham 3-0 Cray Wanderers | Isthmian League - Premier Division |
| 37 | Mon 21 Apr | 52-2 v DartfordCray Wanderers 2-2 Dartford | Isthmian League - Premier Division |
| 38 | Sat 26 Apr | 53-4 v LewesLewes 4-3 Cray Wanderers | Isthmian League - Premier Division |
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