| 1 | Tue 23 Jul 2019 | 190-2 v Sutton UnitedSutton United 2-0 Dulwich Hamlet | Friendly |
| 2 | Sat 3 Aug 2019 | 142-1 v Tonbridge AngelsTonbridge Angels 1-2 Dulwich Hamlet | Vanarama National League South |
| 3 | Tue 6 Aug 2019 | 141-0 v WealdstoneDulwich Hamlet 1-0 Wealdstone | Vanarama National League South |
| 4 | Sat 10 Aug 2019 | 162-1 v St Albans CityDulwich Hamlet 2-1 St Albans City | Vanarama National League South |
| 5 | Tue 13 Aug 2019 | 100-1 v Hemel Hempstead TownHemel Hempstead Town 1-0 Dulwich Hamlet | Vanarama National League South |
| 6 | Sat 17 Aug 2019 | 72-2 v Concord RangersDulwich Hamlet 2-2 Concord Rangers | Vanarama National League South |
| 7 | Sat 24 Aug 2019 | 113-0 v Eastbourne BoroughEastbourne Borough 0-3 Dulwich Hamlet | Vanarama National League South |
| 8 | Mon 26 Aug 2019 | 172-3 v Slough TownDulwich Hamlet 2-3 Slough Town | Vanarama National League South |
| 9 | Sat 31 Aug 2019 | 110-0 v Dorking WanderersDorking Wanderers 0-0 Dulwich Hamlet | Vanarama National League South |
| 10 | Sat 7 Sep 2019 | 161-2 v Braintree TownBraintree Town 2-1 Dulwich Hamlet | Vanarama National League South |
| 11 | Sat 14 Sep 2019 | 112-3 v Hungerford TownDulwich Hamlet 2-3 Hungerford Town | Vanarama National League South |
| 12 | Sat 5 Oct 2019 | 193-0 v Eastbourne BoroughDulwich Hamlet 3-0 Eastbourne Borough | Emirates FA Cup Third Qualifying Round |
| 13 | Sat 26 Oct 2019 | 171-1 v Chelmsford CityChelmsford City 1-1 Dulwich Hamlet | Vanarama National League South |
| 14 | Sat 2 Nov 2019 | 161-3 v Bath CityDulwich Hamlet 1-3 Bath City | Vanarama National League South |
| 15 | Tue 12 Nov 2019 | 150-0 v Welling UnitedWelling United 0-0 Dulwich Hamlet | Vanarama National League South |
| 16 | Sat 16 Nov 2019 | 110-1 v Billericay TownDulwich Hamlet 0-1 Billericay Town | Vanarama National League South |
| 17 | Tue 19 Nov 2019 | 112-3 v Wingate & FinchleyDulwich Hamlet 2-3 Wingate & Finchley | London County Cup Second Round |
| 18 | Sat 23 Nov 2019 | 112-2 v Chippenham TownDulwich Hamlet 2-2 Chippenham Town | Buildbase FA Trophy Third Qualifying Round |
| 19 | Tue 26 Nov 2019 | 172-1 v Chippenham TownChippenham Town 1-2 Dulwich Hamlet | Buildbase FA Trophy Third Qualifying Round Replay |
| 20 | Sat 14 Dec 2019 | 70-1 v HornchurchHornchurch 1-0 Dulwich Hamlet | Buildbase FA Trophy First Round |
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