| 1 | Sat 9 Aug 2014 | 12-2 v Peacehaven & TelscombeLeatherhead 2-2 Peacehaven & Telscombe | Ryman League Premier Division |
| 2 | Wed 20 Aug 2014 | 11-2 v KingstonianLeatherhead 1-2 Kingstonian | Ryman League Premier Division |
| 3 | Sat 23 Aug 2014 | 12-1 v AFC HornchurchLeatherhead 2-1 AFC Hornchurch | Ryman League Premier Division |
| 4 | Mon 25 Aug 2014 | 12-0 v Dulwich HamletLeatherhead 2-0 Dulwich Hamlet | Ryman League Premier Division |
| 5 | Wed 3 Sep 2014 | 10-1 v Billericay TownLeatherhead 0-1 Billericay Town | Ryman League Premier Division |
| 6 | Sat 6 Sep 2014 | 11-2 v Tonbridge AngelsLeatherhead 1-2 Tonbridge Angels | Ryman League Premier Division |
| 7 | Sat 13 Sep 2014 | 11-2 v Faversham TownLeatherhead 1-2 Faversham Town | FA Cup First Qualifying Round |
| 8 | Sat 20 Sep 2014 | 10-2 v Enfield TownLeatherhead 0-2 Enfield Town | Ryman League Premier Division |
| 9 | Wed 24 Sep 2014 | 12-3 v HendonLeatherhead 2-3 Hendon | Ryman League Premier Division |
| 10 | Tue 30 Sep 2014 | 15-1 v Hampton & Richmond BoroughHampton & Richmond Borough 1-5 Leatherhead | Ryman League Premier Division |
| 11 | Sat 4 Oct 2014 | 11-2 v Witham TownLeatherhead 1-2 Witham Town | Ryman League Premier Division |
| 12 | Sat 18 Oct 2014 | 12-0 v Wingate & FinchleyLeatherhead 2-0 Wingate & Finchley | Ryman League Premier Division |
| 13 | Sat 25 Oct 2014 | 10-1 v MargateMargate 1-0 Leatherhead | Ryman League Premier Division |
| 14 | Sat 1 Nov 2014 | 11-1 v Canvey IslandCanvey Island 1-1 Leatherhead | FA Trophy First Qualifying Round |
| 15 | Wed 5 Nov 2014 | 12-2 v Canvey IslandLeatherhead 2-2 Canvey Island | FA Trophy First Qualifying Round Replay |
| 16 | Sat 8 Nov 2014 | 10-1 v LewesLeatherhead 0-1 Lewes | Ryman League Premier Division |
| 17 | Tue 11 Nov 2014 | 11-1 v East Thurrock UnitedEast Thurrock United 1-1 Leatherhead | Ryman League Premier Division |
| 18 | Sat 15 Nov 2014 | 14-1 v WhyteleafeWhyteleafe 1-4 Leatherhead | FA Trophy Second Qualifying Round |
| 19 | Tue 18 Nov 2014 | 11-2 v WhyteleafeWhyteleafe 2-1 Leatherhead | Robert Dyas League Cup Second Round |
| 20 | Tue 2 Dec 2014 | 12-3 v Harrow BoroughHarrow Borough 3-2 Leatherhead | Ryman League Premier Division |
| 21 | Sat 6 Dec 2014 | 12-2 v KingstonianKingstonian 2-2 Leatherhead | Ryman League Premier Division |
| 22 | Tue 9 Dec 2014 | 11-2 v Maidstone UnitedMaidstone United 2-1 Leatherhead | Ryman League Premier Division |
| 23 | Sat 13 Dec 2014 | 13-1 v Grays AthleticLeatherhead 3-1 Grays Athletic | Ryman League Premier Division |
| 24 | Sat 20 Dec 2014 | 12-1 v LeistonLeiston 1-2 Leatherhead | Ryman League Premier Division |
| 25 | Fri 26 Dec 2014 | 10-1 v VCD AthleticLeatherhead 0-1 VCD Athletic | Ryman League Premier Division |
| 26 | Thu 1 Jan 2015 | 11-4 v Dulwich HamletDulwich Hamlet 4-1 Leatherhead | Ryman League Premier Division |
| 27 | Wed 7 Jan 2015 | 14-3 v Bognor Regis TownLeatherhead 4-3 Bognor Regis Town | Ryman League Premier Division |
| 28 | Sat 10 Jan 2015 | 11-1 v Metropolitan PoliceLeatherhead 1-1 Metropolitan Police | Ryman League Premier Division |
| 29 | Sat 17 Jan 2015 | 10-2 v Billericay TownBillericay Town 2-0 Leatherhead | Ryman League Premier Division |
| 30 | Sat 24 Jan 2015 | 13-0 v Tonbridge AngelsTonbridge Angels 0-3 Leatherhead | Ryman League Premier Division |
| 31 | Sat 7 Feb 2015 | 13-2 v Witham TownWitham Town 2-3 Leatherhead | Ryman League Premier Division |
| 32 | Sat 14 Feb 2015 | 13-1 v Hampton & Richmond BoroughLeatherhead 3-1 Hampton & Richmond Borough | Ryman League Premier Division |
| 33 | Sat 21 Feb 2015 | 10-0 v Wingate & FinchleyWingate & Finchley 0-0 Leatherhead | Ryman League Premier Division |
| 34 | Wed 25 Feb 2015 | 14-0 v Bury TownLeatherhead 4-0 Bury Town | Ryman League Premier Division |
| 35 | Sat 28 Feb 2015 | 12-1 v East Thurrock UnitedLeatherhead 2-1 East Thurrock United | Ryman League Premier Division |
| 36 | Tue 3 Mar 2015 | 13-1 v AFC HornchurchAFC Hornchurch 1-3 Leatherhead | Ryman League Premier Division |
| 37 | Sat 7 Mar 2015 | 11-0 v Canvey IslandLeatherhead 1-0 Canvey Island | Ryman League Premier Division |
| 38 | Sat 14 Mar 2015 | 11-3 v Enfield TownEnfield Town 3-1 Leatherhead | Ryman League Premier Division |
| 39 | Sat 21 Mar 2015 | 11-1 v Maidstone UnitedLeatherhead 1-1 Maidstone United | Ryman League Premier Division |
| 40 | Sat 28 Mar 2015 | 10-2 v HendonHendon 2-0 Leatherhead | Ryman League Premier Division |
| 41 | Sat 4 Apr 2015 | 11-0 v LeistonLeatherhead 1-0 Leiston | Ryman League Premier Division |
| 42 | Mon 6 Apr 2015 | 10-2 v VCD AthleticVCD Athletic 2-0 Leatherhead | Ryman League Premier Division |
| 43 | Sat 11 Apr 2015 | 11-0 v MargateLeatherhead 1-0 Margate | Ryman League Premier Division |
| 44 | Sat 18 Apr 2015 | 11-0 v LewesLewes 0-1 Leatherhead | Ryman League Premier Division |
| 45 | Sat 25 Apr 2015 | 10-1 v Harrow BoroughLeatherhead 0-1 Harrow Borough | Ryman League Premier Division |
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