| 1 | Sat 26 Aug | 18 0-2 v Enfield TownEnfield Town 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 2 | Mon 28 Aug | 12 0-3 v Hastings UnitedHastings United 3-0 Cray Wanderers | Isthmian League - Premier Division |
| 3 | Sat 2 Sep | 12 5-1 v NewhavenCray Wanderers 5-1 Newhaven | Emirates FA Cup First Qualifying Round |
| 4 | Sat 9 Sep | 125-1 v Chatham TownChatham Town 1-5 Cray Wanderers | Isthmian League - Premier Division |
| 5 | Sun 17 Sep | 122-2 v RamsgateCray Wanderers 2-2 Ramsgate | Emirates FA Cup Second Qualifying Round |
| 6 | Wed 20 Sep | 122-3 v RamsgateRamsgate 3-2 Cray Wanderers | Emirates FA Cup Second Qualifying Round Replay |
| 7 | Sat 23 Sep | 122-1 v CheshuntCray Wanderers 2-1 Cheshunt | Isthmian League - Premier Division |
| 8 | Sat 7 Oct | 121-0 v Needham MarketNeedham Market 0-1 Cray Wanderers | Isuzu FA Trophy Third Qualifying Round |
| 9 | Sun 15 Oct | 121-4 v HornchurchCray Wanderers 1-4 Hornchurch | Isthmian League - Premier Division |
| 10 | Sat 21 Oct | 121-1 v Potters Bar TownPotters Bar Town 1-1 Cray Wanderers | Isthmian League - Premier Division |
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