| 1 | Sat 9 Aug 2014 | 22-2 v Peacehaven & TelscombeLeatherhead 2-2 Peacehaven & Telscombe | Ryman League Premier Division |
| 2 | Wed 20 Aug 2014 | 21-2 v KingstonianLeatherhead 1-2 Kingstonian | Ryman League Premier Division |
| 3 | Sat 23 Aug 2014 | 22-1 v AFC HornchurchLeatherhead 2-1 AFC Hornchurch | Ryman League Premier Division |
| 4 | Mon 25 Aug 2014 | 22-0 v Dulwich HamletLeatherhead 2-0 Dulwich Hamlet | Ryman League Premier Division |
| 5 | Wed 3 Sep 2014 | 170-1 v Billericay TownLeatherhead 0-1 Billericay Town | Ryman League Premier Division |
| 6 | Sat 6 Sep 2014 | 21-2 v Tonbridge AngelsLeatherhead 1-2 Tonbridge Angels | Ryman League Premier Division |
| 7 | Sat 13 Sep 2014 | 31-2 v Faversham TownLeatherhead 1-2 Faversham Town | FA Cup First Qualifying Round |
| 8 | Sat 20 Sep 2014 | 30-2 v Enfield TownLeatherhead 0-2 Enfield Town | Ryman League Premier Division |
| 9 | Sat 4 Oct 2014 | 181-2 v Witham TownLeatherhead 1-2 Witham Town | Ryman League Premier Division |
| 10 | Sat 18 Oct 2014 | 22-0 v Wingate & FinchleyLeatherhead 2-0 Wingate & Finchley | Ryman League Premier Division |
| 11 | Sat 25 Oct 2014 | 20-1 v MargateMargate 1-0 Leatherhead | Ryman League Premier Division |
| 12 | Sat 1 Nov 2014 | 31-1 v Canvey IslandCanvey Island 1-1 Leatherhead | FA Trophy First Qualifying Round |
| 13 | Wed 5 Nov 2014 | 32-2 v Canvey IslandLeatherhead 2-2 Canvey Island | FA Trophy First Qualifying Round Replay |
| 14 | Tue 11 Nov 2014 | 141-1 v East Thurrock UnitedEast Thurrock United 1-1 Leatherhead | Ryman League Premier Division |
| 15 | Sat 15 Nov 2014 | 34-1 v WhyteleafeWhyteleafe 1-4 Leatherhead | FA Trophy Second Qualifying Round |
| 16 | Tue 18 Nov 2014 | 61-2 v WhyteleafeWhyteleafe 2-1 Leatherhead | Robert Dyas League Cup Second Round |
| 17 | Sat 29 Nov 2014 | 52-3 v Burgess Hill TownBurgess Hill Town 3-2 Leatherhead | FA Trophy Third Qualifying Round |
| 18 | Tue 2 Dec 2014 | 52-3 v Harrow BoroughHarrow Borough 3-2 Leatherhead | Ryman League Premier Division |
| 19 | Sat 6 Dec 2014 | 22-2 v KingstonianKingstonian 2-2 Leatherhead | Ryman League Premier Division |
| 20 | Tue 9 Dec 2014 | 51-2 v Maidstone UnitedMaidstone United 2-1 Leatherhead | Ryman League Premier Division |
| 21 | Sat 13 Dec 2014 | 23-1 v Grays AthleticLeatherhead 3-1 Grays Athletic | Ryman League Premier Division |
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