| 1 | Sat 8 Aug | 101-1 v Wingate & FinchleyWingate & Finchley 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 2 | Tue 11 Aug | 100-0 v CheshuntCray Wanderers 0-0 Cheshunt | Isthmian League - Premier Division |
| 3 | Sat 15 Aug | 101-2 v Carshalton AthleticCarshalton Athletic 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 4 | Sat 22 Aug | 102-1 v Eastbourne BoroughCray Wanderers 2-1 Eastbourne Borough | Isthmian League - Premier Division |
| 5 | Mon 31 Aug | 10 4-1 v Welling UnitedCray Wanderers 4-1 Welling United | Isthmian League - Premier Division |
| 6 | Tue 8 Sep | 101-0 v LewesCray Wanderers 1-0 Lewes | Emirates FA Cup First Qualifying Round Replay |
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