| 1 | Mon 28 Aug | 40-3 v Hastings UnitedHastings United 3-0 Cray Wanderers | Isthmian League - Premier Division |
| 2 | Sat 2 Sep | 155-1 v NewhavenCray Wanderers 5-1 Newhaven | Emirates FA Cup First Qualifying Round |
| 3 | Sat 9 Sep | 155-1 v Chatham TownChatham Town 1-5 Cray Wanderers | Isthmian League - Premier Division |
| 4 | Sun 17 Sep | 152-2 v RamsgateCray Wanderers 2-2 Ramsgate | Emirates FA Cup Second Qualifying Round |
| 5 | Wed 20 Sep | 152-3 v RamsgateRamsgate 3-2 Cray Wanderers | Emirates FA Cup Second Qualifying Round Replay |
| 6 | Tue 26 Sep | 63-2 v Phoenix SportsPhoenix Sports 2-3 Cray Wanderers | Kent Senior Cup First Round |
| 7 | Sat 30 Sep | 50-3 v KingstonianKingstonian 3-0 Cray Wanderers | Isthmian League - Premier Division |
| 8 | Tue 31 Oct | 150-5 v Ebbsfleet UnitedEbbsfleet United 5-0 Cray Wanderers | Kent Senior Cup Second Round |
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