| 1 | Sat 9 Aug 2014 | 60-1 v MargateMargate 1-0 Hampton & Richmond Borough | Ryman League Premier Division |
| 2 | Sat 23 Aug 2014 | 60-4 v Grays AthleticHampton & Richmond Borough 0-4 Grays Athletic | Ryman League Premier Division |
| 3 | Sat 30 Aug 2014 | 62-1 v LewesHampton & Richmond Borough 2-1 Lewes | Ryman League Premier Division |
| 4 | Tue 2 Sep 2014 | 62-1 v Harrow BoroughHarrow Borough 1-2 Hampton & Richmond Borough | Ryman League Premier Division |
| 5 | Sat 6 Sep 2014 | 62-2 v Dulwich HamletDulwich Hamlet 2-2 Hampton & Richmond Borough | Ryman League Premier Division |
| 6 | Tue 9 Sep 2014 | 64-6 v LeistonHampton & Richmond Borough 4-6 Leiston | Ryman League Premier Division |
| 7 | Sat 4 Oct 2014 | 150-2 v Tonbridge AngelsTonbridge Angels 2-0 Hampton & Richmond Borough | Ryman League Premier Division |
| 8 | Tue 7 Oct 2014 | 42-1 v Metropolitan PoliceMetropolitan Police 1-2 Hampton & Richmond Borough | Robert Dyas League Cup First Round |
| 9 | Sat 11 Oct 2014 | 42-1 v VCD AthleticHampton & Richmond Borough 2-1 VCD Athletic | Ryman League Premier Division |
| 10 | Tue 14 Oct 2014 | 40-3 v Metropolitan PoliceMetropolitan Police 3-0 Hampton & Richmond Borough | Ryman League Premier Division |
| 11 | Sat 18 Oct 2014 | 30-3 v Bognor Regis TownBognor Regis Town 3-0 Hampton & Richmond Borough | Ryman League Premier Division |
| 12 | Sat 1 Nov 2014 | 50-3 v Grays AthleticHampton & Richmond Borough 0-3 Grays Athletic | FA Trophy First Qualifying Round |
| 13 | Sat 8 Nov 2014 | 62-0 v Bury TownBury Town 0-2 Hampton & Richmond Borough | Ryman League Premier Division |
| 14 | Sat 15 Nov 2014 | 54-1 v Harlow TownHampton & Richmond Borough 4-1 Harlow Town | Robert Dyas League Cup Second Round |
| 15 | Tue 18 Nov 2014 | 61-2 v Canvey IslandHampton & Richmond Borough 1-2 Canvey Island | Ryman League Premier Division |
| 16 | Tue 9 Dec 2014 | 51-3 v Peacehaven & TelscombeHampton & Richmond Borough 1-3 Peacehaven & Telscombe | Ryman League Premier Division |
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