| 1 | Sat 8 Aug | 2 1-1 v Wingate & FinchleyWingate & Finchley 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 2 | Tue 11 Aug | 20-0 v CheshuntCray Wanderers 0-0 Cheshunt | Isthmian League - Premier Division |
| 3 | Sat 15 Aug | 21-2 v Carshalton AthleticCarshalton Athletic 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 4 | Sat 22 Aug | 22-1 v Eastbourne BoroughCray Wanderers 2-1 Eastbourne Borough | Isthmian League - Premier Division |
| 5 | Mon 31 Aug | 24-1 v Welling UnitedCray Wanderers 4-1 Welling United | Isthmian League - Premier Division |
| 6 | Tue 8 Sep | 21-0 v LewesCray Wanderers 1-0 Lewes | Emirates FA Cup First Qualifying Round Replay |
| 7 | Sat 12 Sep | 22-3 v Enfield TownEnfield Town 3-2 Cray Wanderers | Isthmian League - Premier Division |
| 8 | Tue 15 Sep | 23-3 v St Albans CityCray Wanderers 3-3 St Albans City | Isthmian League - Premier Division |
| 9 | Sat 19 Sep | 21-1 v Maidstone UnitedCray Wanderers 1-1 Maidstone United | Emirates FA Cup Second Qualifying Round |
| 10 | Tue 22 Sep | 22-0 v Maidstone UnitedMaidstone United 0-2 Cray Wanderers | Emirates FA Cup Second Qualifying Round Replay |
| 11 | Sat 26 Sep | 21-1 v CheshuntCheshunt 1-1 Cray Wanderers | FA Trophy Third Qualifying Round |
| 12 | Tue 29 Sep | 25-1 v Maldon & TiptreeMaldon & Tiptree 1-5 Cray Wanderers | Isthmian League - Premier Division |
| 13 | Sat 3 Oct | 23-0 v Chippenham TownCray Wanderers 3-0 Chippenham Town | Emirates FA Cup Third Qualifying Round |
| 14 | Sat 10 Oct | 21-2 v LewesCray Wanderers 1-2 Lewes | Isthmian League - Premier Division |
| 15 | Sat 17 Oct | 2 0-0 v Bedford TownBedford Town 0-0 Cray Wanderers | Emirates FA Cup Fourth Qualifying Round |
| 16 | Tue 20 Oct | 2 2-2 v Bedford TownCray Wanderers 2-2 Bedford Town | Emirates FA Cup Fourth Qualifying Round Replay |
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