| 1 | 10/8/2019 | 141-1 v HorshamHorsham 1-1 Leatherhead | BetVictor Isthmian Premier Division |
| 2 | 13/8/2019 | 122-3 v Haringey BoroughLeatherhead 2-3 Haringey Borough | BetVictor Isthmian Premier Division |
| 3 | 17/8/2019 | 81-1 v Folkestone InvictaFolkestone Invicta 1-1 Leatherhead | BetVictor Isthmian Premier Division |
| 4 | 24/8/2019 | 81-2 v Enfield TownLeatherhead 1-2 Enfield Town | BetVictor Isthmian Premier Division |
| 5 | 26/8/2019 | 80-1 v Carshalton AthleticCarshalton Athletic 1-0 Leatherhead | BetVictor Isthmian Premier Division |
| 6 | 31/8/2019 | 51-4 v LewesLeatherhead 1-4 Lewes | BetVictor Isthmian Premier Division |
| 7 | 28/9/2019 | 121-0 v Bowers & PitseaLeatherhead 1-0 Bowers & Pitsea | BetVictor Isthmian Premier Division |
| 8 | 1/10/2019 | 31-5 v Bognor Regis TownBognor Regis Town 5-1 Leatherhead | BetVictor Isthmian Premier Division |
| 9 | 12/10/2019 | 12 4-1 v MersthamMerstham 1-4 Leatherhead | BetVictor Isthmian Premier Division |
| 10 | 22/10/2019 | 35-2 v Camberley TownLeatherhead 5-2 Camberley Town | Surrey Senior Cup Preliminary Round |
| 11 | 2/11/2019 | 141-0 v Bishop's StortfordBishop's Stortford 0-1 Leatherhead | BetVictor Isthmian Premier Division |
| 12 | 9/11/2019 | 122-1 v Needham MarketNeedham Market 1-2 Leatherhead | Buildbase FA Trophy Second Qualifying Round |
| 13 | 12/11/2019 | 152-1 v Corinthian-CasualsLeatherhead 2-1 Corinthian-Casuals | BetVictor Isthmian Premier Division |
| 14 | 16/11/2019 | 120-3 v East Thurrock UnitedEast Thurrock United 3-0 Leatherhead | BetVictor Isthmian Premier Division |
| 15 | 23/11/2019 | 150-3 v Dorking WanderersLeatherhead 0-3 Dorking Wanderers | Buildbase FA Trophy Third Qualifying Round |
| 16 | 3/12/2019 | 113-2 v RamsgateRamsgate 2-3 Leatherhead | Velocity Trophy |
| 17 | 7/12/2019 | 121-0 v LewesLewes 0-1 Leatherhead | BetVictor Isthmian Premier Division |
| 18 | 10/12/2019 | 8 2-0 v Raynes Park ValeLeatherhead 2-0 Raynes Park Vale | Surrey Senior Cup First Round |
| 19 | 14/12/2019 | 151-0 v Brightlingsea RegentLeatherhead 1-0 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 20 | 21/12/2019 | 120-0 v MargateMargate 0-0 Leatherhead | BetVictor Isthmian Premier Division |
| 21 | 26/12/2019 | 121-0 v Cray WanderersCray Wanderers 0-1 Leatherhead | BetVictor Isthmian Premier Division |
| 22 | 1/1/2020 | 122-1 v Carshalton AthleticLeatherhead 2-1 Carshalton Athletic | BetVictor Isthmian Premier Division |
| 23 | 4/1/2020 | 40-3 v Corinthian-CasualsCorinthian-Casuals 3-0 Leatherhead | BetVictor Isthmian Premier Division |
| 24 | 7/1/2020 | 22-1 v Wingate & FinchleyWingate & Finchley 1-2 Leatherhead | BetVictor Isthmian Premier Division |
| 25 | 11/1/2020 | 21-2 v Bognor Regis TownLeatherhead 1-2 Bognor Regis Town | BetVictor Isthmian Premier Division |
| 26 | 18/1/2020 | 111-1 v HornchurchHornchurch 1-1 Leatherhead | BetVictor Isthmian Premier Division |
| 27 | 21/1/2020 | 60-2 v WorthingWorthing 2-0 Leatherhead | Velocity Trophy |
| 28 | 25/1/2020 | 50-0 v MersthamLeatherhead 0-0 Merstham | BetVictor Isthmian Premier Division |
