| 1 | Sat 15 Aug | 161-2 v Carshalton AthleticCarshalton Athletic 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 2 | Sat 22 Aug | 16 2-1 v Eastbourne BoroughCray Wanderers 2-1 Eastbourne Borough | Isthmian League - Premier Division |
| 3 | Mon 31 Aug | 164-1 v Welling UnitedCray Wanderers 4-1 Welling United | Isthmian League - Premier Division |
| 4 | Sat 12 Sep | 162-3 v Enfield TownEnfield Town 3-2 Cray Wanderers | Isthmian League - Premier Division |
| 5 | Tue 15 Sep | 163-3 v St Albans CityCray Wanderers 3-3 St Albans City | Isthmian League - Premier Division |
| 6 | Tue 29 Sep | 165-1 v Maldon & TiptreeMaldon & Tiptree 1-5 Cray Wanderers | Isthmian League - Premier Division |
| 7 | Sat 10 Oct | 161-2 v LewesCray Wanderers 1-2 Lewes | Isthmian League - Premier Division |
| 8 | Sat 31 Oct | 16 4-1 v Brentwood TownBrentwood Town 1-4 Cray Wanderers | Isthmian League - Premier Division |
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