| 1 | Tue 12 Aug | 81-1 v Folkestone InvictaCray Wanderers 1-1 Folkestone Invicta | Isthmian League - Premier Division |
| 2 | Sat 16 Aug | 83-2 v Wingate & FinchleyCray Wanderers 3-2 Wingate & Finchley | Isthmian League - Premier Division |
| 3 | Sat 23 Aug | 81-0 v Billericay TownBillericay Town 0-1 Cray Wanderers | Isthmian League - Premier Division |
| 4 | Mon 25 Aug | 8 1-5 v Brentwood TownCray Wanderers 1-5 Brentwood Town | Isthmian League - Premier Division |
| 5 | Sat 30 Aug | 82-2 v Hanwell TownCray Wanderers 2-2 Hanwell Town | Emirates FA Cup First Qualifying Round |
| 6 | Sat 6 Sep | 82-2 v LewesLewes 2-2 Cray Wanderers | Isthmian League - Premier Division |
| 7 | Sat 13 Sep | 8 2-2 v Carshalton AthleticCarshalton Athletic 2-2 Cray Wanderers | Isthmian League - Premier Division |
| 8 | Sat 20 Sep | 84-3 v Hashtag UnitedCray Wanderers 4-3 Hashtag United | Isthmian League - Premier Division |
| 9 | Sat 27 Sep | 81-1 v RamsgateRamsgate 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 10 | Tue 30 Sep | 84-2 v Dulwich HamletCray Wanderers 4-2 Dulwich Hamlet | Isthmian League - Premier Division |
| 11 | Sat 11 Oct | 81-1 v Dulwich HamletDulwich Hamlet 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 12 | Sat 18 Oct | 83-3 v Chatham TownChatham Town 3-3 Cray Wanderers | Isthmian League - Premier Division |
| 13 | Tue 21 Oct | 81-1 v St Albans CityCray Wanderers 1-1 St Albans City | Isthmian League - Premier Division |
| 14 | Sat 25 Oct | 8 0-2 v DartfordCray Wanderers 0-2 Dartford | Isthmian League - Premier Division |
| 15 | Sat 1 Nov | 81-1 v CheshuntCheshunt 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 16 | Sat 8 Nov | 80-0 v Chichester CityCray Wanderers 0-0 Chichester City | Isthmian League - Premier Division |
| 17 | Tue 11 Nov | 81-8 v Folkestone InvictaFolkestone Invicta 8-1 Cray Wanderers | Isthmian League - Premier Division |
| 18 | Sat 15 Nov | 8 2-0 v Welling UnitedWelling United 0-2 Cray Wanderers | Isthmian League - Premier Division |
| 19 | Sat 29 Nov | 8 1-1 v Canvey IslandCanvey Island 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 20 | Sat 6 Dec | 8 2-0 v Potters Bar TownPotters Bar Town 0-2 Cray Wanderers | Isthmian League - Premier Division |
| 21 | Fri 12 Dec | 81-2 v WhitehawkCray Wanderers 1-2 Whitehawk | Isthmian League - Premier Division |
| 22 | Sat 20 Dec | 82-1 v Wingate & FinchleyWingate & Finchley 1-2 Cray Wanderers | Isthmian League - Premier Division |
| 23 | Sat 27 Dec | 85-0 v Cray Valley PMCray Wanderers 5-0 Cray Valley PM | Isthmian League - Premier Division |
| 24 | Sat 3 Jan | 84-1 v Brentwood TownBrentwood Town 1-4 Cray Wanderers | Isthmian League - Premier Division |
| 25 | Fri 9 Jan | 80-3 v AveleyCray Wanderers 0-3 Aveley | Isthmian League - Premier Division |
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