| 1 | Sat 25 Sep 2021 | 120-2 v Brightlingsea RegentCray Wanderers 0-2 Brightlingsea Regent | Isthmian League - Premier Division |
| 2 | Wed 29 Sep 2021 | 23-5 v Wingate & FinchleyCray Wanderers 3-5 Wingate & Finchley | Isthmian League - Premier Division |
| 3 | Sat 2 Oct 2021 | 23-1 v Carshalton AthleticCarshalton Athletic 1-3 Cray Wanderers | Isthmian League - Premier Division |
| 4 | Sat 9 Oct 2021 | 21-1 v Haringey BoroughHaringey Borough 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 5 | Sat 23 Oct 2021 | 20-4 v CheshuntCheshunt 4-0 Cray Wanderers | Isthmian League - Premier Division |
| 6 | Tue 9 Nov 2021 | 20-2 v MersthamMerstham 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 7 | Sat 13 Nov 2021 | 2 2-1 v Bedfont SportsCray Wanderers 2-1 Bedfont Sports | Buildbase FA Trophy First Round |
| 8 | Sat 20 Nov 2021 | 2 1-2 v KingstonianKingstonian 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 9 | Wed 24 Nov 2021 | 22-2 v Folkestone InvictaCray Wanderers 2-2 Folkestone Invicta | Isthmian League - Premier Division |
| 10 | Sat 27 Nov 2021 | 22-2 v Ebbsfleet UnitedCray Wanderers 2-2 Ebbsfleet United | Buildbase FA Trophy Second Round |
| 11 | Tue 30 Nov 2021 | 21-1 v Bowers & PitseaBowers & Pitsea 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 12 | Sat 4 Dec 2021 | 20-2 v WorthingWorthing 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 13 | Wed 8 Dec 2021 | 23-1 v HorshamCray Wanderers 3-1 Horsham | Isthmian League - Premier Division |
| 14 | Sat 11 Dec 2021 | 20-1 v Bishop's StortfordCray Wanderers 0-1 Bishop's Stortford | Isthmian League - Premier Division |
| 15 | Mon 27 Dec 2021 | 22-3 v MargateCray Wanderers 2-3 Margate | Isthmian League - Premier Division |
| 16 | Sat 1 Jan 2022 | 23-1 v East Thurrock UnitedEast Thurrock United 1-3 Cray Wanderers | Isthmian League - Premier Division |
| 17 | Mon 3 Jan 2022 | 24-4 v Enfield TownCray Wanderers 4-4 Enfield Town | Isthmian League - Premier Division |
| 18 | Wed 12 Jan 2022 | 20-1 v Bognor Regis TownCray Wanderers 0-1 Bognor Regis Town | Isthmian League - Premier Division |
| 19 | Sat 15 Jan 2022 | 21-2 v Corinthian-CasualsCray Wanderers 1-2 Corinthian-Casuals | Isthmian League - Premier Division |
| 20 | Wed 19 Jan 2022 | 20-0 v LeatherheadCray Wanderers 0-0 Leatherhead | Isthmian League - Premier Division |
| 21 | Sat 22 Jan 2022 | 25-4 v Carshalton AthleticCray Wanderers 5-4 Carshalton Athletic | Isthmian League - Premier Division |
| 22 | Tue 25 Jan 2022 | 20-2 v LewesLewes 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 23 | Sat 29 Jan 2022 | 20-1 v Brightlingsea RegentBrightlingsea Regent 1-0 Cray Wanderers | Isthmian League - Premier Division |
| 24 | Tue 1 Feb 2022 | 23-2 v Potters Bar TownPotters Bar Town 2-3 Cray Wanderers | Isthmian League - Premier Division |
| 25 | Sat 5 Feb 2022 | 2 3-0 v MersthamCray Wanderers 3-0 Merstham | Isthmian League - Premier Division |
| 26 | Sat 12 Feb 2022 | 22-2 v Wingate & FinchleyWingate & Finchley 2-2 Cray Wanderers | Isthmian League - Premier Division |
| 27 | Tue 15 Feb 2022 | 20-1 v Folkestone InvictaFolkestone Invicta 1-0 Cray Wanderers | Isthmian League - Premier Division |
| 28 | Sat 5 Mar 2022 | 21-1 v CheshuntCray Wanderers 1-1 Cheshunt | Isthmian League - Premier Division |
| 29 | Wed 9 Mar 2022 | 21-2 v Haringey BoroughCray Wanderers 1-2 Haringey Borough | Isthmian League - Premier Division |
| 30 | Sat 12 Mar 2022 | 23-2 v Bognor Regis TownBognor Regis Town 2-3 Cray Wanderers | Isthmian League - Premier Division |
| 31 | Sun 20 Mar 2022 | 23-4 v Bowers & PitseaCray Wanderers 3-4 Bowers & Pitsea | Isthmian League - Premier Division |
| 32 | Sat 26 Mar 2022 | 21-2 v KingstonianCray Wanderers 1-2 Kingstonian | Isthmian League - Premier Division |
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