| 1 | Sat 9 Aug | 52-0 v Canvey IslandCray Wanderers 2-0 Canvey Island | Isthmian League - Premier Division |
| 2 | Tue 12 Aug | 51-1 v Folkestone InvictaCray Wanderers 1-1 Folkestone Invicta | Isthmian League - Premier Division |
| 3 | Sat 16 Aug | 53-2 v Wingate & FinchleyCray Wanderers 3-2 Wingate & Finchley | Isthmian League - Premier Division |
| 4 | Sat 6 Sep | 52-2 v LewesLewes 2-2 Cray Wanderers | Isthmian League - Premier Division |
| 5 | Sat 13 Sep | 5 2-2 v Carshalton AthleticCarshalton Athletic 2-2 Cray Wanderers | Isthmian League - Premier Division |
| 6 | Sat 20 Sep | 54-3 v Hashtag UnitedCray Wanderers 4-3 Hashtag United | Isthmian League - Premier Division |
| 7 | Sat 27 Sep | 51-1 v RamsgateRamsgate 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 8 | Tue 30 Sep | 54-2 v Dulwich HamletCray Wanderers 4-2 Dulwich Hamlet | Isthmian League - Premier Division |
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