| 1 | Tue 5 Aug 2014 | 23-3 v Tooting & Mitcham UnitedDulwich Hamlet 3-3 Tooting & Mitcham United | Friendly |
| 2 | Sat 9 Aug 2014 | 23-2 v Harrow BoroughDulwich Hamlet 3-2 Harrow Borough | Ryman League Premier Division |
| 3 | Mon 11 Aug 2014 | 21-1 v KingstonianKingstonian 1-1 Dulwich Hamlet | Ryman League Premier Division |
| 4 | Sat 16 Aug 2014 | 22-0 v LeistonLeiston 0-2 Dulwich Hamlet | Ryman League Premier Division |
| 5 | Tue 19 Aug 2014 | 23-1 v Peacehaven & TelscombeDulwich Hamlet 3-1 Peacehaven & Telscombe | Ryman League Premier Division |
| 6 | Sat 23 Aug 2014 | 22-0 v LewesDulwich Hamlet 2-0 Lewes | Ryman League Premier Division |
| 7 | Sat 30 Aug 2014 | 21-2 v Billericay TownBillericay Town 2-1 Dulwich Hamlet | Ryman League Premier Division |
| 8 | Tue 2 Sep 2014 | 22-1 v MargateDulwich Hamlet 2-1 Margate | Ryman League Premier Division |
| 9 | Sat 6 Sep 2014 | 22-2 v Hampton & Richmond BoroughDulwich Hamlet 2-2 Hampton & Richmond Borough | Ryman League Premier Division |
| 10 | Wed 10 Sep 2014 | 20-1 v Grays AthleticGrays Athletic 1-0 Dulwich Hamlet | Ryman League Premier Division |
| 11 | Sat 13 Sep 2014 | 20-3 v WorthingDulwich Hamlet 0-3 Worthing | FA Cup First Qualifying Round |
| 12 | Sat 20 Sep 2014 | 122-0 v AFC HornchurchDulwich Hamlet 2-0 AFC Hornchurch | Ryman League Premier Division |
| 13 | Tue 23 Sep 2014 | 123-3 v Wingate & FinchleyDulwich Hamlet 3-3 Wingate & Finchley | Ryman League Premier Division |
| 14 | Tue 14 Oct 2014 | 52-2 v Walton & HershamDulwich Hamlet 2-2 Walton & Hersham | Robert Dyas League Cup First Round |
| 15 | Sat 1 Nov 2014 | 163-0 v Chalfont St PeterDulwich Hamlet 3-0 Chalfont St Peter | FA Trophy First Qualifying Round |
| 16 | Wed 12 Nov 2014 | 121-1 v Maidstone UnitedMaidstone United 1-1 Dulwich Hamlet | Ryman League Premier Division |
| 17 | Sat 15 Nov 2014 | 20-2 v Metropolitan PoliceMetropolitan Police 2-0 Dulwich Hamlet | FA Trophy Second Qualifying Round |
| 18 | Tue 25 Nov 2014 | 152-2 v East Thurrock UnitedEast Thurrock United 2-2 Dulwich Hamlet | Ryman League Premier Division |
| 19 | Sat 29 Nov 2014 | 52-1 v KingstonianDulwich Hamlet 2-1 Kingstonian | Ryman League Premier Division |
| 20 | Sat 14 Feb 2015 | 23-1 v Bury TownBury Town 1-3 Dulwich Hamlet | Ryman League Premier Division |
| 21 | Sat 7 Mar 2015 | 51-2 v VCD AthleticDulwich Hamlet 1-2 VCD Athletic | Ryman League Premier Division |
| 22 | Sat 14 Mar 2015 | 50-1 v AFC HornchurchAFC Hornchurch 1-0 Dulwich Hamlet | Ryman League Premier Division |
| 23 | Sat 11 Apr 2015 | 22-2 v HendonHendon 2-2 Dulwich Hamlet | Ryman League Premier Division |
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