| 1 | Sat 10 Aug | 42-0 v Hashtag UnitedHashtag United 0-2 Cray Wanderers | Isthmian League - Premier Division |
| 2 | Tue 13 Aug | 4 0-2 v Cray Valley PMCray Wanderers 0-2 Cray Valley PM | Isthmian League - Premier Division |
| 3 | Sat 17 Aug | 41-3 v HendonHendon 3-1 Cray Wanderers | Isthmian League - Premier Division |
| 4 | Sat 24 Aug | 4 1-3 v LewesCray Wanderers 1-3 Lewes | Isthmian League - Premier Division |
| 5 | Mon 26 Aug | 41-2 v Dulwich HamletDulwich Hamlet 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 6 | Tue 3 Sep | 48-0 v Larkfield & New HytheCray Wanderers 8-0 Larkfield & New Hythe | Emirates FA Cup First Qualifying Round Replay |
| 7 | Sat 7 Sep | 4 0-0 v HorshamCray Wanderers 0-0 Horsham | Isthmian League - Premier Division |
| 8 | Sat 14 Sep | 41-1 v Wingate & FinchleyCray Wanderers 1-1 Wingate & Finchley | Emirates FA Cup Second Qualifying Round |
| 9 | Tue 17 Sep | 41-0 v Wingate & FinchleyWingate & Finchley 0-1 Cray Wanderers | Emirates FA Cup Second Qualifying Round Replay |
| 10 | Sat 21 Sep | 41-3 v Bognor Regis TownBognor Regis Town 3-1 Cray Wanderers | Isthmian League - Premier Division |
| 11 | Sat 28 Sep | 43-0 v Hastings UnitedCray Wanderers 3-0 Hastings United | Emirates FA Cup Third Qualifying Round |
| 12 | Sat 5 Oct | 41-1 v Brentwood TownBrentwood Town 1-1 Cray Wanderers | Isuzu FA Trophy Third Qualifying Round |
| 13 | Tue 15 Oct | 41-4 v Chatham TownCray Wanderers 1-4 Chatham Town | Isthmian League - Premier Division |
| 14 | Sat 19 Oct | 40-0 v Hastings UnitedCray Wanderers 0-0 Hastings United | Isthmian League - Premier Division |
| 15 | Tue 29 Oct | 42-2 v Phoenix SportsCray Wanderers 2-2 Phoenix Sports | Kent Senior Cup Second Round |
| 16 | Sat 2 Nov | 43-0 v Hashtag UnitedCray Wanderers 3-0 Hashtag United | Isthmian League - Premier Division |
| 17 | Tue 5 Nov | 41-2 v Cray Valley PMCray Valley PM 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 18 | Sat 9 Nov | 40-1 v Folkestone InvictaFolkestone Invicta 1-0 Cray Wanderers | Isthmian League - Premier Division |
| 19 | Sat 16 Nov | 44-0 v Potters Bar TownPotters Bar Town 0-4 Cray Wanderers | Isthmian League - Premier Division |
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