| 1 | Fri 8 Nov 2019 | 31-4 v Carlisle UnitedDulwich Hamlet 1-4 Carlisle United | Emirates FA Cup First Round |
| 2 | Tue 12 Nov 2019 | 30-0 v Welling UnitedWelling United 0-0 Dulwich Hamlet | Vanarama National League South |
| 3 | Sat 16 Nov 2019 | 30-1 v Billericay TownDulwich Hamlet 0-1 Billericay Town | Vanarama National League South |
| 4 | Tue 19 Nov 2019 | 52-3 v Wingate & FinchleyDulwich Hamlet 2-3 Wingate & Finchley | London County Cup Second Round |
| 5 | Sat 23 Nov 2019 | 32-2 v Chippenham TownDulwich Hamlet 2-2 Chippenham Town | Buildbase FA Trophy Third Qualifying Round |
| 6 | Tue 26 Nov 2019 | 3 2-1 v Chippenham TownChippenham Town 1-2 Dulwich Hamlet | Buildbase FA Trophy Third Qualifying Round Replay |
| 7 | Sat 30 Nov 2019 | 31-2 v Oxford CityOxford City 2-1 Dulwich Hamlet | Vanarama National League South |
| 8 | Sat 7 Dec 2019 | 31-1 v DartfordDulwich Hamlet 1-1 Dartford | Vanarama National League South |
| 9 | Sat 14 Dec 2019 | 30-1 v HornchurchHornchurch 1-0 Dulwich Hamlet | Buildbase FA Trophy First Round |
| 10 | Sat 21 Dec 2019 | 164-1 v Hungerford TownHungerford Town 1-4 Dulwich Hamlet | Vanarama National League South |
| 11 | Sat 28 Dec 2019 | 151-4 v Maidstone UnitedMaidstone United 4-1 Dulwich Hamlet | Vanarama National League South |
| 12 | Sat 11 Jan 2020 | 15 1-1 v WeymouthWeymouth 1-1 Dulwich Hamlet | Vanarama National League South |
| 13 | Sat 7 Mar 2020 | 31-2 v WealdstoneWealdstone 2-1 Dulwich Hamlet | Vanarama National League South |
| 14 | Sat 14 Mar 2020 | 32-1 v Hemel Hempstead TownDulwich Hamlet 2-1 Hemel Hempstead Town | Vanarama National League South |
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