| 1 | Sat 4 Nov | 123-1 v Wingate & FinchleyWingate & Finchley 1-3 Cray Wanderers | Isthmian League - Premier Division |
| 2 | Wed 8 Nov | 124-2 v Tooting & Mitcham UnitedCray Wanderers 4-2 Tooting & Mitcham United | London County Cup First Round |
| 3 | Sat 11 Nov | 12 1-0 v Carshalton AthleticCray Wanderers 1-0 Carshalton Athletic | Isthmian League - Premier Division |
| 4 | Sat 18 Nov | 121-4 v Weston-super-MareWeston-super-Mare 4-1 Cray Wanderers | Isuzu FA Trophy Second Round |
| 5 | Sat 25 Nov | 121-1 v Dulwich HamletCray Wanderers 1-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 6 | Sat 16 Dec | 120-1 v Hashtag UnitedHashtag United 1-0 Cray Wanderers | Isthmian League - Premier Division |
| 7 | Tue 26 Dec | 120-0 v MargateCray Wanderers 0-0 Margate | Isthmian League - Premier Division |
| 8 | Fri 29 Dec | 122-0 v Enfield TownCray Wanderers 2-0 Enfield Town | Isthmian League - Premier Division |
| 9 | Mon 1 Jan | 12 0-0 v Hastings UnitedCray Wanderers 0-0 Hastings United | Isthmian League - Premier Division |
| 10 | Sat 6 Jan | 121-1 v LewesCray Wanderers 1-1 Lewes | Isthmian League - Premier Division |
| 11 | Tue 9 Jan | 121-2 v Bognor Regis TownBognor Regis Town 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 12 | Sat 13 Jan | 120-6 v Billericay TownBillericay Town 6-0 Cray Wanderers | Isthmian League - Premier Division |
| 13 | Wed 24 Jan | 123-0 v FisherCray Wanderers 3-0 Fisher | London County Cup Second Round |
| 14 | Sat 27 Jan | 121-0 v Wingate & FinchleyCray Wanderers 1-0 Wingate & Finchley | Isthmian League - Premier Division |
| 15 | Sat 3 Feb | 32-1 v Carshalton AthleticCarshalton Athletic 1-2 Cray Wanderers | Isthmian League - Premier Division |
| 16 | Tue 6 Feb | 32-2 v Folkestone InvictaFolkestone Invicta 2-2 Cray Wanderers | Isthmian League - Premier Division |
| 17 | Sun 11 Feb | 31-1 v Concord RangersCray Wanderers 1-1 Concord Rangers | Isthmian League - Premier Division |
| 18 | Sat 17 Feb | 31-0 v CheshuntCheshunt 0-1 Cray Wanderers | Isthmian League - Premier Division |
| 19 | Wed 13 Mar | 31-2 v Potters Bar TownCray Wanderers 1-2 Potters Bar Town | Isthmian League - Premier Division |
| 20 | Sat 16 Mar | 34-0 v Haringey BoroughHaringey Borough 0-4 Cray Wanderers | Isthmian League - Premier Division |
| 21 | Sun 24 Mar | 30-1 v Folkestone InvictaCray Wanderers 0-1 Folkestone Invicta | Isthmian League - Premier Division |
| 22 | Fri 29 Mar | 32-2 v Chatham TownCray Wanderers 2-2 Chatham Town | Isthmian League - Premier Division |
| 23 | Mon 1 Apr | 31-1 v MargateMargate 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 24 | Fri 5 Apr | 31-3 v Hashtag UnitedCray Wanderers 1-3 Hashtag United | Isthmian League - Premier Division |
| 25 | Tue 9 Apr | 30-2 v HornchurchHornchurch 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 26 | Sat 13 Apr | 30-2 v HorshamHorsham 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 27 | Tue 16 Apr | 31-2 v DartfordCray Wanderers 1-2 Dartford | London County Cup Quarter Final |
| 28 | Sat 20 Apr | 31-5 v Bognor Regis TownCray Wanderers 1-5 Bognor Regis Town | Isthmian League - Premier Division |
| 29 | Sat 27 Apr | 36-2 v Dulwich HamletDulwich Hamlet 2-6 Cray Wanderers | Isthmian League - Premier Division |
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