| 1 | Sat 24 Aug | 201-3 v LewesCray Wanderers 1-3 Lewes | Isthmian League - Premier Division |
| 2 | Mon 26 Aug | 201-2 v Dulwich HamletDulwich Hamlet 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 3 | Sat 31 Aug | 201-1 v Larkfield & New HytheLarkfield & New Hythe 1-1 Cray Wanderers | Emirates FA Cup First Qualifying Round |
| 4 | Tue 3 Sep | 208-0 v Larkfield & New HytheCray Wanderers 8-0 Larkfield & New Hythe | Emirates FA Cup First Qualifying Round Replay |
| 5 | Sat 7 Sep | 20-0 v HorshamCray Wanderers 0-0 Horsham | Isthmian League - Premier Division |
| 6 | Sat 14 Sep | 21-1 v Wingate & FinchleyCray Wanderers 1-1 Wingate & Finchley | Emirates FA Cup Second Qualifying Round |
| 7 | Tue 17 Sep | 21-0 v Wingate & FinchleyWingate & Finchley 0-1 Cray Wanderers | Emirates FA Cup Second Qualifying Round Replay |
| 8 | Sat 19 Oct | 20-0 v Hastings UnitedCray Wanderers 0-0 Hastings United | Isthmian League - Premier Division |
| 9 | Tue 29 Oct | 22-2 v Phoenix SportsCray Wanderers 2-2 Phoenix Sports | Kent Senior Cup Second Round |
| 10 | Tue 19 Nov | 24-7 v Erith TownCray Wanderers 4-7 Erith Town | London Senior Cup Second Round |
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