| 1 | Sat 12 Aug | 20-1 v LewesLewes 1-0 Cray Wanderers | Isthmian League - Premier Division |
| 2 | Wed 16 Aug | 2 1-3 v HorshamCray Wanderers 1-3 Horsham | Isthmian League - Premier Division |
| 3 | Sat 19 Aug | 20-1 v Billericay TownCray Wanderers 0-1 Billericay Town | Isthmian League - Premier Division |
| 4 | Sat 26 Aug | 2 0-2 v Enfield TownEnfield Town 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 5 | Sat 2 Sep | 25-1 v NewhavenCray Wanderers 5-1 Newhaven | Emirates FA Cup First Qualifying Round |
| 6 | Tue 26 Sep | 23-2 v Phoenix SportsPhoenix Sports 2-3 Cray Wanderers | Kent Senior Cup First Round |
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