| 1 | Sat 9 Aug | 22-0 v Canvey IslandCray Wanderers 2-0 Canvey Island | Isthmian League - Premier Division |
| 2 | Tue 12 Aug | 21-1 v Folkestone InvictaCray Wanderers 1-1 Folkestone Invicta | Isthmian League - Premier Division |
| 3 | Sat 16 Aug | 23-2 v Wingate & FinchleyCray Wanderers 3-2 Wingate & Finchley | Isthmian League - Premier Division |
| 4 | Sat 23 Aug | 2 1-0 v Billericay TownBillericay Town 0-1 Cray Wanderers | Isthmian League - Premier Division |
| 5 | Mon 25 Aug | 21-5 v Brentwood TownCray Wanderers 1-5 Brentwood Town | Isthmian League - Premier Division |
| 6 | Sat 6 Sep | 22-2 v LewesLewes 2-2 Cray Wanderers | Isthmian League - Premier Division |
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