| 1 | Sat 30 Aug | 92-2 v Hanwell TownCray Wanderers 2-2 Hanwell Town | Emirates FA Cup First Qualifying Round |
| 2 | Tue 2 Sep | 9 0-1 v Hanwell TownHanwell Town 1-0 Cray Wanderers | Emirates FA Cup First Qualifying Round Replay |
| 3 | Sat 6 Sep | 92-2 v LewesLewes 2-2 Cray Wanderers | Isthmian League - Premier Division |
| 4 | Sat 13 Sep | 92-2 v Carshalton AthleticCarshalton Athletic 2-2 Cray Wanderers | Isthmian League - Premier Division |
| 5 | Sat 20 Sep | 94-3 v Hashtag UnitedCray Wanderers 4-3 Hashtag United | Isthmian League - Premier Division |
| 6 | Sat 27 Sep | 91-1 v RamsgateRamsgate 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 7 | Tue 30 Sep | 94-2 v Dulwich HamletCray Wanderers 4-2 Dulwich Hamlet | Isthmian League - Premier Division |
| 8 | Sat 11 Oct | 9 1-1 v Dulwich HamletDulwich Hamlet 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 9 | Sat 18 Oct | 9 3-3 v Chatham TownChatham Town 3-3 Cray Wanderers | Isthmian League - Premier Division |
| 10 | Sat 25 Oct | 90-2 v DartfordCray Wanderers 0-2 Dartford | Isthmian League - Premier Division |
| 11 | Sat 1 Nov | 91-1 v CheshuntCheshunt 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 12 | Sat 8 Nov | 90-0 v Chichester CityCray Wanderers 0-0 Chichester City | Isthmian League - Premier Division |
| 13 | Tue 11 Nov | 9 1-8 v Folkestone InvictaFolkestone Invicta 8-1 Cray Wanderers | Isthmian League - Premier Division |
| 14 | Sat 15 Nov | 92-0 v Welling UnitedWelling United 0-2 Cray Wanderers | Isthmian League - Premier Division |
| 15 | Sat 6 Dec | 9 2-0 v Potters Bar TownPotters Bar Town 0-2 Cray Wanderers | Isthmian League - Premier Division |
| 16 | Fri 12 Dec | 91-2 v WhitehawkCray Wanderers 1-2 Whitehawk | Isthmian League - Premier Division |
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