| 1 | Sat 13 Jul | 100-4 v SheffieldCray Wanderers 0-4 Sheffield | Friendly |
| 2 | Sat 10 Aug | 102-0 v Hashtag UnitedHashtag United 0-2 Cray Wanderers | Isthmian League - Premier Division |
| 3 | Tue 13 Aug | 10 0-2 v Cray Valley PMCray Wanderers 0-2 Cray Valley PM | Isthmian League - Premier Division |
| 4 | Sat 17 Aug | 101-3 v HendonHendon 3-1 Cray Wanderers | Isthmian League - Premier Division |
| 5 | Sat 24 Aug | 101-3 v LewesCray Wanderers 1-3 Lewes | Isthmian League - Premier Division |
| 6 | Mon 26 Aug | 101-2 v Dulwich HamletDulwich Hamlet 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 7 | Sat 31 Aug | 101-1 v Larkfield & New HytheLarkfield & New Hythe 1-1 Cray Wanderers | Emirates FA Cup First Qualifying Round |
| 8 | Tue 3 Sep | 108-0 v Larkfield & New HytheCray Wanderers 8-0 Larkfield & New Hythe | Emirates FA Cup First Qualifying Round Replay |
| 9 | Sat 7 Sep | 100-0 v HorshamCray Wanderers 0-0 Horsham | Isthmian League - Premier Division |
| 10 | Sat 14 Sep | 101-1 v Wingate & FinchleyCray Wanderers 1-1 Wingate & Finchley | Emirates FA Cup Second Qualifying Round |
| 11 | Tue 17 Sep | 101-0 v Wingate & FinchleyWingate & Finchley 0-1 Cray Wanderers | Emirates FA Cup Second Qualifying Round Replay |
| 12 | Sat 21 Sep | 101-3 v Bognor Regis TownBognor Regis Town 3-1 Cray Wanderers | Isthmian League - Premier Division |
| 13 | Tue 24 Sep | 10 2-1 v Chatham TownChatham Town 1-2 Cray Wanderers | Kent Senior Cup First Round |
| 14 | Sat 28 Sep | 103-0 v Hastings UnitedCray Wanderers 3-0 Hastings United | Emirates FA Cup Third Qualifying Round |
| 15 | Sat 5 Oct | 101-1 v Brentwood TownBrentwood Town 1-1 Cray Wanderers | Isuzu FA Trophy Third Qualifying Round |
| 16 | Sat 12 Oct | 100-1 v Tonbridge AngelsCray Wanderers 0-1 Tonbridge Angels | Emirates FA Cup Fourth Qualifying Round |
| 17 | Tue 15 Oct | 10 1-4 v Chatham TownCray Wanderers 1-4 Chatham Town | Isthmian League - Premier Division |
| 18 | Sat 19 Oct | 100-0 v Hastings UnitedCray Wanderers 0-0 Hastings United | Isthmian League - Premier Division |
| 19 | Tue 22 Oct | 100-0 v WhitehawkCray Wanderers 0-0 Whitehawk | Isthmian League - Premier Division |
| 20 | Sat 26 Oct | 101-0 v CheshuntCheshunt 0-1 Cray Wanderers | Isthmian League - Premier Division |
| 21 | Tue 29 Oct | 102-2 v Phoenix SportsCray Wanderers 2-2 Phoenix Sports | Kent Senior Cup Second Round |
| 22 | Sat 2 Nov | 103-0 v Hashtag UnitedCray Wanderers 3-0 Hashtag United | Isthmian League - Premier Division |
| 23 | Sat 9 Nov | 100-1 v Folkestone InvictaFolkestone Invicta 1-0 Cray Wanderers | Isthmian League - Premier Division |
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