| 1 | Sat 9 Aug | 12-0 v Canvey IslandCray Wanderers 2-0 Canvey Island | Isthmian League - Premier Division |
| 2 | Tue 12 Aug | 11-1 v Folkestone InvictaCray Wanderers 1-1 Folkestone Invicta | Isthmian League - Premier Division |
| 3 | Sat 16 Aug | 13-2 v Wingate & FinchleyCray Wanderers 3-2 Wingate & Finchley | Isthmian League - Premier Division |
| 4 | Sat 23 Aug | 11-0 v Billericay TownBillericay Town 0-1 Cray Wanderers | Isthmian League - Premier Division |
| 5 | Mon 25 Aug | 11-5 v Brentwood TownCray Wanderers 1-5 Brentwood Town | Isthmian League - Premier Division |
| 6 | Sat 6 Sep | 12-2 v LewesLewes 2-2 Cray Wanderers | Isthmian League - Premier Division |
| 7 | Sat 13 Sep | 12-2 v Carshalton AthleticCarshalton Athletic 2-2 Cray Wanderers | Isthmian League - Premier Division |
| 8 | Sat 20 Sep | 14-3 v Hashtag UnitedCray Wanderers 4-3 Hashtag United | Isthmian League - Premier Division |
| 9 | Sat 27 Sep | 11-1 v RamsgateRamsgate 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 10 | Tue 30 Sep | 14-2 v Dulwich HamletCray Wanderers 4-2 Dulwich Hamlet | Isthmian League - Premier Division |
| 11 | Sat 11 Oct | 11-1 v Dulwich HamletDulwich Hamlet 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 12 | Sat 18 Oct | 13-3 v Chatham TownChatham Town 3-3 Cray Wanderers | Isthmian League - Premier Division |
| 13 | Tue 21 Oct | 11-1 v St Albans CityCray Wanderers 1-1 St Albans City | Isthmian League - Premier Division |
| 14 | Sat 25 Oct | 10-2 v DartfordCray Wanderers 0-2 Dartford | Isthmian League - Premier Division |
| 15 | Sat 15 Nov | 12-0 v Welling UnitedWelling United 0-2 Cray Wanderers | Isthmian League - Premier Division |
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