| 1 | Sat 3 Nov 2018 | 5 2-2 v Bognor Regis TownLeatherhead 2-2 Bognor Regis Town | Bostik League Premier Division |
| 2 | Sat 10 Nov 2018 | 140-1 v MargateLeatherhead 0-1 Margate | Bostik League Premier Division |
| 3 | Wed 14 Nov 2018 | 14 2-1 v KingstonianLeatherhead 2-1 Kingstonian | Bostik League Premier Division |
| 4 | Sat 17 Nov 2018 | 144-1 v Enfield TownLeatherhead 4-1 Enfield Town | Bostik League Premier Division |
| 5 | Wed 21 Nov 2018 | 143-0 v Burgess Hill TownLeatherhead 3-0 Burgess Hill Town | Bostik League Premier Division |
| 6 | Sat 24 Nov 2018 | 52-0 v Tonbridge AngelsTonbridge Angels 0-2 Leatherhead | Bostik League Premier Division |
| 7 | Wed 28 Nov 2018 | 5 1-2 v Corinthian-CasualsLeatherhead 1-2 Corinthian-Casuals | Bostik League Premier Division |
| 8 | Sat 1 Dec 2018 | 140-1 v LewesLewes 1-0 Leatherhead | Bostik League Premier Division |
| 9 | Sat 8 Dec 2018 | 0-1 v BarrowBarrow 1-0 Maidstone United | National League |
| 10 | Sat 29 Dec 2018 | 21-0 v Boreham WoodBoreham Wood 0-1 Maidstone United | National League |
| 11 | Tue 1 Jan 2019 | 20-1 v Dover AthleticMaidstone United 0-1 Dover Athletic | National League |
| 12 | Sat 5 Jan 2019 | 22-1 v Hartlepool UnitedHartlepool United 1-2 Maidstone United | National League |
| 13 | Tue 15 Jan 2019 | 22-4 v Maidenhead UnitedMaidstone United 2-4 Maidenhead United | National League |
| 14 | Sat 9 Feb 2019 | 3-2 v Truro CityBillericay Town 3-2 Truro City | National League South |
| 15 | Sat 16 Feb 2019 | 2-0 v Eastbourne BoroughBillericay Town 2-0 Eastbourne Borough | National League South |
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