| 1 | Sat 13 Jul | 80-4 v SheffieldCray Wanderers 0-4 Sheffield | Friendly |
| 2 | Sat 10 Aug | 162-0 v Hashtag UnitedHashtag United 0-2 Cray Wanderers | Isthmian League - Premier Division |
| 3 | Tue 13 Aug | 16 0-2 v Cray Valley PMCray Wanderers 0-2 Cray Valley PM | Isthmian League - Premier Division |
| 4 | Sat 17 Aug | 161-3 v HendonHendon 3-1 Cray Wanderers | Isthmian League - Premier Division |
| 5 | Sat 24 Aug | 161-3 v LewesCray Wanderers 1-3 Lewes | Isthmian League - Premier Division |
| 6 | Mon 26 Aug | 161-2 v Dulwich HamletDulwich Hamlet 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 7 | Sat 31 Aug | 16 1-1 v Larkfield & New HytheLarkfield & New Hythe 1-1 Cray Wanderers | Emirates FA Cup First Qualifying Round |
| 8 | Tue 3 Sep | 168-0 v Larkfield & New HytheCray Wanderers 8-0 Larkfield & New Hythe | Emirates FA Cup First Qualifying Round Replay |
| 9 | Sat 7 Sep | 160-0 v HorshamCray Wanderers 0-0 Horsham | Isthmian League - Premier Division |
| 10 | Sat 14 Sep | 161-1 v Wingate & FinchleyCray Wanderers 1-1 Wingate & Finchley | Emirates FA Cup Second Qualifying Round |
| 11 | Tue 17 Sep | 16 1-0 v Wingate & FinchleyWingate & Finchley 0-1 Cray Wanderers | Emirates FA Cup Second Qualifying Round Replay |
| 12 | Sat 21 Sep | 161-3 v Bognor Regis TownBognor Regis Town 3-1 Cray Wanderers | Isthmian League - Premier Division |
| 13 | Sat 12 Oct | 160-1 v Tonbridge AngelsCray Wanderers 0-1 Tonbridge Angels | Emirates FA Cup Fourth Qualifying Round |
| 14 | Tue 15 Oct | 161-4 v Chatham TownCray Wanderers 1-4 Chatham Town | Isthmian League - Premier Division |
| 15 | Sat 19 Oct | 160-0 v Hastings UnitedCray Wanderers 0-0 Hastings United | Isthmian League - Premier Division |
| 16 | Tue 22 Oct | 160-0 v WhitehawkCray Wanderers 0-0 Whitehawk | Isthmian League - Premier Division |
| 17 | Sat 26 Oct | 161-0 v CheshuntCheshunt 0-1 Cray Wanderers | Isthmian League - Premier Division |
| 18 | Sat 2 Nov | 163-0 v Hashtag UnitedCray Wanderers 3-0 Hashtag United | Isthmian League - Premier Division |
| 19 | Tue 5 Nov | 161-2 v Cray Valley PMCray Valley PM 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 20 | Sat 9 Nov | 16 0-1 v Folkestone InvictaFolkestone Invicta 1-0 Cray Wanderers | Isthmian League - Premier Division |
| 21 | Sat 16 Nov | 164-0 v Potters Bar TownPotters Bar Town 0-4 Cray Wanderers | Isthmian League - Premier Division |
| 22 | Sat 23 Nov | 16 0-2 v Canvey IslandCanvey Island 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 23 | Sat 30 Nov | 16 1-1 v Carshalton AthleticCray Wanderers 1-1 Carshalton Athletic | Isthmian League - Premier Division |
| 24 | Sat 7 Dec | 161-0 v Bowers & PitseaBowers & Pitsea 0-1 Cray Wanderers | Isthmian League - Premier Division |
| 25 | Tue 10 Dec | 16 1-0 v Chichester CityCray Wanderers 1-0 Chichester City | Isthmian League - Premier Division |
| 26 | Sat 21 Dec | 161-1 v Billericay TownCray Wanderers 1-1 Billericay Town | Isthmian League - Premier Division |
| 27 | Sat 28 Dec | 161-0 v HendonCray Wanderers 1-0 Hendon | Isthmian League - Premier Division |
| 28 | Wed 1 Jan | 161-0 v Dulwich HamletCray Wanderers 1-0 Dulwich Hamlet | Isthmian League - Premier Division |
| 29 | Sat 25 Jan | 160-2 v WhitehawkWhitehawk 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 30 | Tue 28 Jan | 160-1 v Wingate & FinchleyWingate & Finchley 1-0 Cray Wanderers | Isthmian League - Premier Division |
| 31 | Sat 8 Feb | 164-1 v Chatham TownChatham Town 1-4 Cray Wanderers | Isthmian League - Premier Division |
| 32 | Sat 15 Feb | 162-1 v CheshuntCray Wanderers 2-1 Cheshunt | Isthmian League - Premier Division |
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