| 1 | 12/9/2020 | 163-0 v RamsgateRamsgate 0-3 Chipstead | Emirates FA Cup Preliminary Round |
| 2 | 19/9/2020 | 150-2 v Bracknell TownBracknell Town 2-0 Chipstead | Isthmian League - South Central Division |
| 3 | 22/9/2020 | 121-1 v Deal TownChipstead 1-1 Deal Town | Emirates FA Cup First Qualifying Round |
| 4 | 26/9/2020 | 10 1-4 v WestfieldChipstead 1-4 Westfield | Isthmian League - South Central Division |
| 5 | 3/10/2020 | 121-0 v East Grinstead TownChipstead 1-0 East Grinstead Town | Emirates FA Cup Second Qualifying Round |
| 6 | 6/10/2020 | 123-2 v Harlow TownHarlow Town 2-3 Chipstead | Isthmian League - South Central Division |
| 7 | 10/10/2020 | 150-5 v Bedfont SportsChipstead 0-5 Bedfont Sports | Isthmian League - South Central Division |
| 8 | 13/10/2020 | 120-0 v Hayes & Yeading UnitedHayes & Yeading United 0-0 Chipstead | Emirates FA Cup Third Qualifying Round |
| 9 | 17/10/2020 | 141-2 v Three BridgesChipstead 1-2 Three Bridges | Buildbase FA Trophy Second Qualifying Round |
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