| 1 | Sat 6 Dec | 192-0 v Potters Bar TownPotters Bar Town 0-2 Cray Wanderers | Isthmian League - Premier Division |
| 2 | Fri 12 Dec | 19 1-2 v WhitehawkCray Wanderers 1-2 Whitehawk | Isthmian League - Premier Division |
| 3 | Sat 20 Dec | 19 2-1 v Wingate & FinchleyWingate & Finchley 1-2 Cray Wanderers | Isthmian League - Premier Division |
| 4 | Sat 27 Dec | 195-0 v Cray Valley PMCray Wanderers 5-0 Cray Valley PM | Isthmian League - Premier Division |
| 5 | Sat 3 Jan | 194-1 v Brentwood TownBrentwood Town 1-4 Cray Wanderers | Isthmian League - Premier Division |
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