| 1 | Sat 9 Oct 2021 | 12-1 v Dulwich HamletDulwich Hamlet 1-2 Billericay Town | Vanarama National League South |
| 2 | Sat 11 Dec 2021 | 10-1 v Bishop's StortfordCray Wanderers 0-1 Bishop's Stortford | Isthmian League - Premier Division |
| 3 | Sat 18 Dec 2021 | 11-3 v DartfordCray Wanderers 1-3 Dartford | Buildbase FA Trophy Third Round |
| 4 | Mon 27 Dec 2021 | 12-3 v MargateCray Wanderers 2-3 Margate | Isthmian League - Premier Division |
| 5 | Sat 1 Jan 2022 | 13-1 v East Thurrock UnitedEast Thurrock United 1-3 Cray Wanderers | Isthmian League - Premier Division |
| 6 | Mon 3 Jan 2022 | 1 4-4 v Enfield TownCray Wanderers 4-4 Enfield Town | Isthmian League - Premier Division |
| 7 | Wed 12 Jan 2022 | 10-1 v Bognor Regis TownCray Wanderers 0-1 Bognor Regis Town | Isthmian League - Premier Division |
| 8 | Sat 15 Jan 2022 | 11-2 v Corinthian-CasualsCray Wanderers 1-2 Corinthian-Casuals | Isthmian League - Premier Division |
| 9 | Wed 19 Jan 2022 | 10-0 v LeatherheadCray Wanderers 0-0 Leatherhead | Isthmian League - Premier Division |
| 10 | Sat 22 Jan 2022 | 15-4 v Carshalton AthleticCray Wanderers 5-4 Carshalton Athletic | Isthmian League - Premier Division |
| 11 | Tue 25 Jan 2022 | 10-2 v LewesLewes 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 12 | Sat 29 Jan 2022 | 10-1 v Brightlingsea RegentBrightlingsea Regent 1-0 Cray Wanderers | Isthmian League - Premier Division |
| 13 | Tue 1 Feb 2022 | 13-2 v Potters Bar TownPotters Bar Town 2-3 Cray Wanderers | Isthmian League - Premier Division |
| 14 | Sat 5 Feb 2022 | 13-0 v MersthamCray Wanderers 3-0 Merstham | Isthmian League - Premier Division |
| 15 | Sat 12 Feb 2022 | 12-2 v Wingate & FinchleyWingate & Finchley 2-2 Cray Wanderers | Isthmian League - Premier Division |
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