| 1 | Tue 12 Aug | 81-1 v Folkestone InvictaCray Wanderers 1-1 Folkestone Invicta | Isthmian League - Premier Division |
| 2 | Sat 16 Aug | 83-2 v Wingate & FinchleyCray Wanderers 3-2 Wingate & Finchley | Isthmian League - Premier Division |
| 3 | Sat 23 Aug | 81-0 v Billericay TownBillericay Town 0-1 Cray Wanderers | Isthmian League - Premier Division |
| 4 | Mon 25 Aug | 8 1-5 v Brentwood TownCray Wanderers 1-5 Brentwood Town | Isthmian League - Premier Division |
| 5 | Sat 30 Aug | 82-2 v Hanwell TownCray Wanderers 2-2 Hanwell Town | Emirates FA Cup First Qualifying Round |
| 6 | Sat 6 Sep | 82-2 v LewesLewes 2-2 Cray Wanderers | Isthmian League - Premier Division |
| 7 | Sat 13 Sep | 8 2-2 v Carshalton AthleticCarshalton Athletic 2-2 Cray Wanderers | Isthmian League - Premier Division |
| 8 | Sat 20 Sep | 84-3 v Hashtag UnitedCray Wanderers 4-3 Hashtag United | Isthmian League - Premier Division |
| 9 | Sat 27 Sep | 81-1 v RamsgateRamsgate 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 10 | Tue 30 Sep | 84-2 v Dulwich HamletCray Wanderers 4-2 Dulwich Hamlet | Isthmian League - Premier Division |
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