| 1 | 22/8/2020 | 34-0 v Epsom & EwellLeatherhead 4-0 Epsom & Ewell | Friendly |
| 2 | 31/8/2020 | 180-2 v Dorking WanderersLeatherhead 0-2 Dorking Wanderers | Friendly |
| 3 | 2/9/2020 | 30-0 v FarnboroughFarnborough 0-0 Leatherhead | Friendly |
| 4 | 8/9/2020 | 34-3 v WhyteleafeWhyteleafe 3-4 Leatherhead | Friendly |
| 5 | 12/9/2020 | 30-1 v Beaconsfield TownLeatherhead 0-1 Beaconsfield Town | Friendly |
| 6 | 19/9/2020 | 31-1 v HorshamLeatherhead 1-1 Horsham | Isthmian League - Premier Division |
| 7 | 26/9/2020 | 30-7 v Bowers & PitseaBowers & Pitsea 7-0 Leatherhead | Isthmian League - Premier Division |
| 8 | 28/9/2020 | 3 1-0 v Haringey BoroughHaringey Borough 0-1 Leatherhead | Isthmian League - Premier Division |
| 9 | 3/10/2020 | 30-0 v MargateLeatherhead 0-0 Margate | Isthmian League - Premier Division |
| 10 | 6/10/2020 | 34-3 v WorthingLeatherhead 4-3 Worthing | Isthmian League - Premier Division |
| 11 | 10/10/2020 | 30-1 v Enfield TownEnfield Town 1-0 Leatherhead | Isthmian League - Premier Division |
| 12 | 17/10/2020 | 32-0 v Folkestone InvictaLeatherhead 2-0 Folkestone Invicta | Isthmian League - Premier Division |
| 13 | 20/10/2020 | 30-3 v Brightlingsea RegentBrightlingsea Regent 3-0 Leatherhead | Isthmian League - Premier Division |
| 14 | 24/10/2020 | 30-0 v Corinthian-CasualsCorinthian-Casuals 0-0 Leatherhead | Isthmian League - Premier Division |
| 15 | 31/10/2020 | 33-1 v Potters Bar TownLeatherhead 3-1 Potters Bar Town | Buildbase FA Trophy Third Qualifying Round |
| 16 | 8/12/2020 | 30-1 v Felixstowe & Walton UnitedLeatherhead 0-1 Felixstowe & Walton United | Buildbase FA Trophy First Round |
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