| 1 | Sat 7 Sep 2019 | 5 1-2 v Braintree TownBraintree Town 2-1 Dulwich Hamlet | Vanarama National League South |
| 2 | Sat 14 Sep 2019 | 62-3 v Hungerford TownDulwich Hamlet 2-3 Hungerford Town | Vanarama National League South |
| 3 | Sat 21 Sep 2019 | 66-1 v Bognor Regis TownDulwich Hamlet 6-1 Bognor Regis Town | Emirates FA Cup Second Qualifying Round |
| 4 | Sat 28 Sep 2019 | 22-2 v Chippenham TownChippenham Town 2-2 Dulwich Hamlet | Vanarama National League South |
| 5 | Sat 5 Oct 2019 | 23-0 v Eastbourne BoroughDulwich Hamlet 3-0 Eastbourne Borough | Emirates FA Cup Third Qualifying Round |
| 6 | Sat 12 Oct 2019 | 22-2 v WeymouthDulwich Hamlet 2-2 Weymouth | Vanarama National League South |
| 7 | Sat 19 Oct 2019 | 22-1 v Havant & WaterloovilleHavant & Waterlooville 1-2 Dulwich Hamlet | Emirates FA Cup Fourth Qualifying Round |
| 8 | Sat 26 Oct 2019 | 21-1 v Chelmsford CityChelmsford City 1-1 Dulwich Hamlet | Vanarama National League South |
| 9 | Sat 2 Nov 2019 | 21-3 v Bath CityDulwich Hamlet 1-3 Bath City | Vanarama National League South |
| 10 | Fri 8 Nov 2019 | 21-4 v Carlisle UnitedDulwich Hamlet 1-4 Carlisle United | Emirates FA Cup First Round |
| 11 | Tue 12 Nov 2019 | 20-0 v Welling UnitedWelling United 0-0 Dulwich Hamlet | Vanarama National League South |
| 12 | Sat 16 Nov 2019 | 20-1 v Billericay TownDulwich Hamlet 0-1 Billericay Town | Vanarama National League South |
| 13 | Sat 7 Dec 2019 | 2 1-1 v DartfordDulwich Hamlet 1-1 Dartford | Vanarama National League South |
| 14 | Sat 14 Dec 2019 | 50-1 v HornchurchHornchurch 1-0 Dulwich Hamlet | Buildbase FA Trophy First Round |
| 15 | Sat 21 Dec 2019 | 24-1 v Hungerford TownHungerford Town 1-4 Dulwich Hamlet | Vanarama National League South |
| 16 | Sat 22 Feb 2020 | 2 2-3 v Bath CityBath City 3-2 Dulwich Hamlet | Vanarama National League South |
| 17 | Sat 29 Feb 2020 | 2 0-1 v Tonbridge AngelsDulwich Hamlet 0-1 Tonbridge Angels | Vanarama National League South |
| 18 | Sat 7 Mar 2020 | 21-2 v WealdstoneWealdstone 2-1 Dulwich Hamlet | Vanarama National League South |
| 19 | Sat 14 Mar 2020 | 22-1 v Hemel Hempstead TownDulwich Hamlet 2-1 Hemel Hempstead Town | Vanarama National League South |
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