| 1 | 19/9/2020 | 161-0 v UxbridgeChertsey Town 1-0 Uxbridge | Isthmian League - South Central Division |
| 2 | 22/9/2020 | 160-0 v LeatherheadChertsey Town 0-0 Leatherhead | Emirates FA Cup First Qualifying Round |
| 3 | 3/10/2020 | 150-2 v Haringey BoroughHaringey Borough 2-0 Chertsey Town | Emirates FA Cup Second Qualifying Round |
| 4 | 6/10/2020 | 161-2 v Bracknell TownChertsey Town 1-2 Bracknell Town | Isthmian League - South Central Division |
| 5 | 10/10/2020 | 73-1 v NorthwoodNorthwood 1-3 Chertsey Town | Isthmian League - South Central Division |
| 6 | 13/10/2020 | 72-2 v South ParkSouth Park 2-2 Chertsey Town | Isthmian League - South Central Division |
| 7 | 17/10/2020 | 151-2 v BerkhamstedChertsey Town 1-2 Berkhamsted | Buildbase FA Trophy Second Qualifying Round |
| 8 | 20/10/2020 | 140-3 v MarlowChertsey Town 0-3 Marlow | Isthmian League - South Central Division |
| 9 | 24/10/2020 | 74-1 v Hertford TownChertsey Town 4-1 Hertford Town | Isthmian League - South Central Division |
| 10 | 27/10/2020 | 73-0 v Ashford Town (Middx)Ashford Town (Middx) 0-3 Chertsey Town | Isthmian League - South Central Division |
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