| 1 | Sat 9 Aug | 12 2-0 v Canvey IslandCray Wanderers 2-0 Canvey Island | Isthmian League - Premier Division |
| 2 | Tue 12 Aug | 121-1 v Folkestone InvictaCray Wanderers 1-1 Folkestone Invicta | Isthmian League - Premier Division |
| 3 | Sat 16 Aug | 123-2 v Wingate & FinchleyCray Wanderers 3-2 Wingate & Finchley | Isthmian League - Premier Division |
| 4 | Sat 23 Aug | 12 1-0 v Billericay TownBillericay Town 0-1 Cray Wanderers | Isthmian League - Premier Division |
| 5 | Mon 25 Aug | 121-5 v Brentwood TownCray Wanderers 1-5 Brentwood Town | Isthmian League - Premier Division |
| 6 | Tue 2 Sep | 120-1 v Hanwell TownHanwell Town 1-0 Cray Wanderers | Emirates FA Cup First Qualifying Round Replay |
| 7 | Sat 6 Sep | 122-2 v LewesLewes 2-2 Cray Wanderers | Isthmian League - Premier Division |
| 8 | Tue 9 Sep | 12 0-2 v Herne BayCray Wanderers 0-2 Herne Bay | Kent Senior Cup |
| 9 | Sat 13 Sep | 122-2 v Carshalton AthleticCarshalton Athletic 2-2 Cray Wanderers | Isthmian League - Premier Division |
| 10 | Sat 20 Sep | 124-3 v Hashtag UnitedCray Wanderers 4-3 Hashtag United | Isthmian League - Premier Division |
| 11 | Tue 7 Oct | 124-5 v AFC WimbledonCray Wanderers 4-5 AFC Wimbledon | London Senior Cup |
| 12 | Sat 11 Oct | 12 1-1 v Dulwich HamletDulwich Hamlet 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 13 | Sat 18 Oct | 12 3-3 v Chatham TownChatham Town 3-3 Cray Wanderers | Isthmian League - Premier Division |
| 14 | Sat 8 Nov | 120-0 v Chichester CityCray Wanderers 0-0 Chichester City | Isthmian League - Premier Division |
| 15 | Tue 11 Nov | 12 1-8 v Folkestone InvictaFolkestone Invicta 8-1 Cray Wanderers | Isthmian League - Premier Division |
| 16 | Sat 15 Nov | 122-0 v Welling UnitedWelling United 0-2 Cray Wanderers | Isthmian League - Premier Division |
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