| 1 | Sat 15 Aug 2020 | 21-0 v VCD AthleticVCD Athletic 0-1 Leatherhead | Friendly |
| 2 | Sat 22 Aug 2020 | 2 4-0 v Epsom & EwellLeatherhead 4-0 Epsom & Ewell | Friendly |
| 3 | Mon 31 Aug 2020 | 20-2 v Dorking WanderersLeatherhead 0-2 Dorking Wanderers | Friendly |
| 4 | Wed 2 Sep 2020 | 50-0 v FarnboroughFarnborough 0-0 Leatherhead | Friendly |
| 5 | Sat 5 Sep 2020 | 55-0 v Staines TownLeatherhead 5-0 Staines Town | Friendly |
| 6 | Tue 8 Sep 2020 | 54-3 v WhyteleafeWhyteleafe 3-4 Leatherhead | Friendly |
| 7 | Sat 12 Sep 2020 | 50-1 v Beaconsfield TownLeatherhead 0-1 Beaconsfield Town | Friendly |
| 8 | Sat 19 Sep 2020 | 21-1 v HorshamLeatherhead 1-1 Horsham | Isthmian League - Premier Division |
| 9 | Tue 22 Sep 2020 | 20-0 v Chertsey TownChertsey Town 0-0 Leatherhead | Emirates FA Cup First Qualifying Round |
| 10 | Sat 26 Sep 2020 | 20-7 v Bowers & PitseaBowers & Pitsea 7-0 Leatherhead | Isthmian League - Premier Division |
| 11 | Mon 28 Sep 2020 | 51-0 v Haringey BoroughHaringey Borough 0-1 Leatherhead | Isthmian League - Premier Division |
| 12 | Sat 3 Oct 2020 | 50-0 v MargateLeatherhead 0-0 Margate | Isthmian League - Premier Division |
| 13 | Tue 6 Oct 2020 | 54-3 v WorthingLeatherhead 4-3 Worthing | Isthmian League - Premier Division |
| 14 | Sat 10 Oct 2020 | 50-1 v Enfield TownEnfield Town 1-0 Leatherhead | Isthmian League - Premier Division |
| 15 | Sat 17 Oct 2020 | 52-0 v Folkestone InvictaLeatherhead 2-0 Folkestone Invicta | Isthmian League - Premier Division |
| 16 | Tue 20 Oct 2020 | 50-3 v Brightlingsea RegentBrightlingsea Regent 3-0 Leatherhead | Isthmian League - Premier Division |
| 17 | Sat 24 Oct 2020 | 50-0 v Corinthian-CasualsCorinthian-Casuals 0-0 Leatherhead | Isthmian League - Premier Division |
| 18 | Sat 31 Oct 2020 | 53-1 v Potters Bar TownLeatherhead 3-1 Potters Bar Town | Buildbase FA Trophy Third Qualifying Round |
| 19 | Tue 8 Dec 2020 | 50-1 v Felixstowe & Walton UnitedLeatherhead 0-1 Felixstowe & Walton United | Buildbase FA Trophy First Round |
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