| 1 | Tue 9 Jul 2019 | 50-2 v Colchester UnitedDulwich Hamlet 0-2 Colchester United | Friendly |
| 2 | Fri 12 Jul 2019 | 52-1 v ChesterChester 1-2 Dulwich Hamlet | Friendly |
| 3 | Sat 13 Jul 2019 | 154-2 v MarineMarine 2-4 Dulwich Hamlet | Friendly |
| 4 | Tue 16 Jul 2019 | 51-1 v BromleyDulwich Hamlet 1-1 Bromley | Friendly |
| 5 | Sat 3 Aug 2019 | 52-1 v Tonbridge AngelsTonbridge Angels 1-2 Dulwich Hamlet | Vanarama National League South |
| 6 | Tue 6 Aug 2019 | 51-0 v WealdstoneDulwich Hamlet 1-0 Wealdstone | Vanarama National League South |
| 7 | Sat 10 Aug 2019 | 52-1 v St Albans CityDulwich Hamlet 2-1 St Albans City | Vanarama National League South |
| 8 | Tue 13 Aug 2019 | 50-1 v Hemel Hempstead TownHemel Hempstead Town 1-0 Dulwich Hamlet | Vanarama National League South |
| 9 | Sat 17 Aug 2019 | 52-2 v Concord RangersDulwich Hamlet 2-2 Concord Rangers | Vanarama National League South |
| 10 | Sat 24 Aug 2019 | 5 3-0 v Eastbourne BoroughEastbourne Borough 0-3 Dulwich Hamlet | Vanarama National League South |
| 11 | Sat 31 Aug 2019 | 50-0 v Dorking WanderersDorking Wanderers 0-0 Dulwich Hamlet | Vanarama National League South |
| 12 | Tue 3 Sep 2019 | 50-1 v Maidstone UnitedDulwich Hamlet 0-1 Maidstone United | Vanarama National League South |
| 13 | Sat 14 Sep 2019 | 52-3 v Hungerford TownDulwich Hamlet 2-3 Hungerford Town | Vanarama National League South |
| 14 | Sat 21 Sep 2019 | 56-1 v Bognor Regis TownDulwich Hamlet 6-1 Bognor Regis Town | Emirates FA Cup Second Qualifying Round |
| 15 | Sat 28 Sep 2019 | 5 2-2 v Chippenham TownChippenham Town 2-2 Dulwich Hamlet | Vanarama National League South |
| 16 | Sat 5 Oct 2019 | 53-0 v Eastbourne BoroughDulwich Hamlet 3-0 Eastbourne Borough | Emirates FA Cup Third Qualifying Round |
| 17 | Fri 8 Nov 2019 | 51-4 v Carlisle UnitedDulwich Hamlet 1-4 Carlisle United | Emirates FA Cup First Round |
| 18 | Tue 12 Nov 2019 | 5 0-0 v Welling UnitedWelling United 0-0 Dulwich Hamlet | Vanarama National League South |
| 19 | Sat 16 Nov 2019 | 50-1 v Billericay TownDulwich Hamlet 0-1 Billericay Town | Vanarama National League South |
| 20 | Sat 23 Nov 2019 | 5 2-2 v Chippenham TownDulwich Hamlet 2-2 Chippenham Town | Buildbase FA Trophy Third Qualifying Round |
| 21 | Tue 26 Nov 2019 | 5 2-1 v Chippenham TownChippenham Town 1-2 Dulwich Hamlet | Buildbase FA Trophy Third Qualifying Round Replay |
| 22 | Sat 30 Nov 2019 | 51-2 v Oxford CityOxford City 2-1 Dulwich Hamlet | Vanarama National League South |
| 23 | Sat 21 Dec 2019 | 5 4-1 v Hungerford TownHungerford Town 1-4 Dulwich Hamlet | Vanarama National League South |
| 24 | Thu 26 Dec 2019 | 51-2 v Hampton & Richmond BoroughDulwich Hamlet 1-2 Hampton & Richmond Borough | Vanarama National League South |
| 25 | Sat 28 Dec 2019 | 51-4 v Maidstone UnitedMaidstone United 4-1 Dulwich Hamlet | Vanarama National League South |
| 26 | Sat 22 Feb 2020 | 62-3 v Bath CityBath City 3-2 Dulwich Hamlet | Vanarama National League South |
| 27 | Sat 29 Feb 2020 | 60-1 v Tonbridge AngelsDulwich Hamlet 0-1 Tonbridge Angels | Vanarama National League South |
| 28 | Sat 7 Mar 2020 | 61-2 v WealdstoneWealdstone 2-1 Dulwich Hamlet | Vanarama National League South |
| 29 | Sat 14 Mar 2020 | 62-1 v Hemel Hempstead TownDulwich Hamlet 2-1 Hemel Hempstead Town | Vanarama National League South |
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