| 1 | Sat 3 Nov 2018 | 92-2 v Bognor Regis TownLeatherhead 2-2 Bognor Regis Town | Bostik League Premier Division |
| 2 | Mon 5 Nov 2018 | 92-2 v Carshalton AthleticCarshalton Athletic 2-2 Leatherhead | Surrey Senior Cup First Round |
| 3 | Sat 17 Nov 2018 | 184-1 v Enfield TownLeatherhead 4-1 Enfield Town | Bostik League Premier Division |
| 4 | Wed 21 Nov 2018 | 153-0 v Burgess Hill TownLeatherhead 3-0 Burgess Hill Town | Bostik League Premier Division |
| 5 | Sat 24 Nov 2018 | 122-0 v Tonbridge AngelsTonbridge Angels 0-2 Leatherhead | Bostik League Premier Division |
| 6 | Wed 28 Nov 2018 | 121-2 v Corinthian-CasualsLeatherhead 1-2 Corinthian-Casuals | Bostik League Premier Division |
| 7 | Sat 1 Dec 2018 | 100-1 v LewesLewes 1-0 Leatherhead | Bostik League Premier Division |
| 8 | Sat 8 Dec 2018 | 150-1 v Brightlingsea RegentLeatherhead 0-1 Brightlingsea Regent | Bostik League Premier Division |
| 9 | Tue 11 Dec 2018 | 102-0 v MersthamMerstham 0-2 Leatherhead | Bostik League Premier Division |
| 10 | Sat 15 Dec 2018 | 102-2 v Harlow TownHarlow Town 2-2 Leatherhead | Bostik League Premier Division |
| 11 | Sat 22 Dec 2018 | 100-2 v Folkestone InvictaFolkestone Invicta 2-0 Leatherhead | Bostik League Premier Division |
| 12 | Wed 26 Dec 2018 | 91-0 v Carshalton AthleticLeatherhead 1-0 Carshalton Athletic | Bostik League Premier Division |
| 13 | Sat 29 Dec 2018 | 9 0-2 v Dorking WanderersDorking Wanderers 2-0 Leatherhead | Bostik League Premier Division |
| 14 | Sat 5 Jan 2019 | 102-1 v Potters Bar TownLeatherhead 2-1 Potters Bar Town | Bostik League Premier Division |
| 15 | Sat 12 Jan 2019 | 111-2 v Corinthian-CasualsCorinthian-Casuals 2-1 Leatherhead | Bostik League Premier Division |
| 16 | Sat 19 Jan 2019 | 102-1 v WorthingLeatherhead 2-1 Worthing | Bostik League Premier Division |
| 17 | Sat 26 Jan 2019 | 101-1 v MargateMargate 1-1 Leatherhead | Bostik League Premier Division |
| 18 | Sat 2 Feb 2019 | 122-1 v Wingate & FinchleyLeatherhead 2-1 Wingate & Finchley | Bostik League Premier Division |
| 19 | Tue 5 Feb 2019 | 92-0 v WhitehawkWhitehawk 0-2 Leatherhead | Bostik League Premier Division |
| 20 | Sat 9 Feb 2019 | 101-0 v Bishop's StortfordLeatherhead 1-0 Bishop's Stortford | Bostik League Premier Division |
| 21 | Sat 16 Feb 2019 | 103-0 v Haringey BoroughHaringey Borough 0-3 Leatherhead | Bostik League Premier Division |
| 22 | Sat 23 Feb 2019 | 101-2 v AFC HornchurchLeatherhead 1-2 AFC Hornchurch | Bostik League Premier Division |
| 23 | Sat 2 Mar 2019 | 10 0-1 v MersthamLeatherhead 0-1 Merstham | Bostik League Premier Division |
| 24 | Sat 9 Mar 2019 | 93-0 v Burgess Hill TownBurgess Hill Town 0-3 Leatherhead | Bostik League Premier Division |
| 25 | Sat 16 Mar 2019 | 90-0 v Folkestone InvictaLeatherhead 0-0 Folkestone Invicta | Bostik League Premier Division |
| 26 | Sat 23 Mar 2019 | 94-0 v Bognor Regis TownBognor Regis Town 0-4 Leatherhead | Bostik League Premier Division |
| 27 | Sat 30 Mar 2019 | 91-0 v Enfield TownEnfield Town 0-1 Leatherhead | Bostik League Premier Division |
| 28 | Sat 6 Apr 2019 | 91-0 v Tonbridge AngelsLeatherhead 1-0 Tonbridge Angels | Bostik League Premier Division |
| 29 | Sat 13 Apr 2019 | 91-1 v LewesLeatherhead 1-1 Lewes | Bostik League Premier Division |
| 30 | Sat 20 Apr 2019 | 10 0-1 v Brightlingsea RegentBrightlingsea Regent 1-0 Leatherhead | Bostik League Premier Division |
| 31 | Sat 27 Apr 2019 | 94-0 v KingstonianKingstonian 0-4 Leatherhead | Bostik League Premier Division |
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