| 1 | Sat 25 Nov | 51-1 v Dulwich HamletCray Wanderers 1-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 2 | Sun 10 Dec | 53-3 v Haringey BoroughCray Wanderers 3-3 Haringey Borough | Isthmian League - Premier Division |
| 3 | Sat 16 Dec | 5 0-1 v Hashtag UnitedHashtag United 1-0 Cray Wanderers | Isthmian League - Premier Division |
| 4 | Sat 13 Jan | 60-6 v Billericay TownBillericay Town 6-0 Cray Wanderers | Isthmian League - Premier Division |
| 5 | Wed 24 Jan | 63-0 v FisherCray Wanderers 3-0 Fisher | London County Cup Second Round |
| 6 | Sat 27 Jan | 51-0 v Wingate & FinchleyCray Wanderers 1-0 Wingate & Finchley | Isthmian League - Premier Division |
| 7 | Sat 3 Feb | 62-1 v Carshalton AthleticCarshalton Athletic 1-2 Cray Wanderers | Isthmian League - Premier Division |
| 8 | Tue 6 Feb | 62-2 v Folkestone InvictaFolkestone Invicta 2-2 Cray Wanderers | Isthmian League - Premier Division |
| 9 | Sun 11 Feb | 61-1 v Concord RangersCray Wanderers 1-1 Concord Rangers | Isthmian League - Premier Division |
| 10 | Sat 17 Feb | 61-0 v CheshuntCheshunt 0-1 Cray Wanderers | Isthmian League - Premier Division |
| 11 | Wed 21 Feb | 6 2-1 v Canvey IslandCray Wanderers 2-1 Canvey Island | Isthmian League - Premier Division |
| 12 | Sat 24 Feb | 61-0 v KingstonianCray Wanderers 1-0 Kingstonian | Isthmian League - Premier Division |
| 13 | Tue 27 Feb | 60-2 v WhitehawkWhitehawk 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 14 | Wed 13 Mar | 6 1-2 v Potters Bar TownCray Wanderers 1-2 Potters Bar Town | Isthmian League - Premier Division |
| 15 | Sat 16 Mar | 64-0 v Haringey BoroughHaringey Borough 0-4 Cray Wanderers | Isthmian League - Premier Division |
| 16 | Fri 29 Mar | 62-2 v Chatham TownCray Wanderers 2-2 Chatham Town | Isthmian League - Premier Division |
| 17 | Mon 1 Apr | 6 1-1 v MargateMargate 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 18 | Fri 5 Apr | 61-3 v Hashtag UnitedCray Wanderers 1-3 Hashtag United | Isthmian League - Premier Division |
| 19 | Tue 9 Apr | 60-2 v HornchurchHornchurch 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 20 | Sat 13 Apr | 6 0-2 v HorshamHorsham 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 21 | Tue 16 Apr | 61-2 v DartfordCray Wanderers 1-2 Dartford | London County Cup Quarter Final |
| 22 | Sat 27 Apr | 66-2 v Dulwich HamletDulwich Hamlet 2-6 Cray Wanderers | Isthmian League - Premier Division |
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