| 1 | Tue 9 Jul 2019 | 10-2 v Colchester UnitedDulwich Hamlet 0-2 Colchester United | Friendly |
| 2 | Sat 13 Jul 2019 | 14-2 v MarineMarine 2-4 Dulwich Hamlet | Friendly |
| 3 | Tue 16 Jul 2019 | 11-1 v BromleyDulwich Hamlet 1-1 Bromley | Friendly |
| 4 | Tue 23 Jul 2019 | 10-2 v Sutton UnitedSutton United 2-0 Dulwich Hamlet | Friendly |
| 5 | Sat 5 Oct 2019 | 13-0 v Eastbourne BoroughDulwich Hamlet 3-0 Eastbourne Borough | Emirates FA Cup Third Qualifying Round |
| 6 | Sat 12 Oct 2019 | 12-2 v WeymouthDulwich Hamlet 2-2 Weymouth | Vanarama National League South |
| 7 | Sat 19 Oct 2019 | 12-1 v Havant & WaterloovilleHavant & Waterlooville 1-2 Dulwich Hamlet | Emirates FA Cup Fourth Qualifying Round |
| 8 | Sat 26 Oct 2019 | 11-1 v Chelmsford CityChelmsford City 1-1 Dulwich Hamlet | Vanarama National League South |
| 9 | Sat 2 Nov 2019 | 11-3 v Bath CityDulwich Hamlet 1-3 Bath City | Vanarama National League South |
| 10 | Fri 8 Nov 2019 | 11-4 v Carlisle UnitedDulwich Hamlet 1-4 Carlisle United | Emirates FA Cup First Round |
| 11 | Tue 12 Nov 2019 | 10-0 v Welling UnitedWelling United 0-0 Dulwich Hamlet | Vanarama National League South |
| 12 | Sat 16 Nov 2019 | 10-1 v Billericay TownDulwich Hamlet 0-1 Billericay Town | Vanarama National League South |
| 13 | Sat 23 Nov 2019 | 12-2 v Chippenham TownDulwich Hamlet 2-2 Chippenham Town | Buildbase FA Trophy Third Qualifying Round |
| 14 | Tue 26 Nov 2019 | 12-1 v Chippenham TownChippenham Town 1-2 Dulwich Hamlet | Buildbase FA Trophy Third Qualifying Round Replay |
| 15 | Wed 1 Jan 2020 | 13-0 v Hampton & Richmond BoroughHampton & Richmond Borough 0-3 Dulwich Hamlet | Vanarama National League South |
| 16 | Sat 4 Jan 2020 | 16-0 v Braintree TownDulwich Hamlet 6-0 Braintree Town | Vanarama National League South |
| 17 | Sat 11 Jan 2020 | 11-1 v WeymouthWeymouth 1-1 Dulwich Hamlet | Vanarama National League South |
| 18 | Sat 18 Jan 2020 | 11-1 v Chippenham TownDulwich Hamlet 1-1 Chippenham Town | Vanarama National League South |
| 19 | Tue 21 Jan 2020 | 11-3 v Havant & WaterloovilleDulwich Hamlet 1-3 Havant & Waterlooville | Vanarama National League South |
| 20 | Sat 25 Jan 2020 | 10-1 v DartfordDartford 1-0 Dulwich Hamlet | Vanarama National League South |
| 21 | Sat 1 Feb 2020 | 15-3 v Chelmsford CityDulwich Hamlet 5-3 Chelmsford City | Vanarama National League South |
| 22 | Sat 8 Feb 2020 | 10-0 v Havant & WaterloovilleHavant & Waterlooville 0-0 Dulwich Hamlet | Vanarama National League South |
| 23 | Sat 15 Feb 2020 | 10-1 v Welling UnitedDulwich Hamlet 0-1 Welling United | Vanarama National League South |
| 24 | Sat 22 Feb 2020 | 12-3 v Bath CityBath City 3-2 Dulwich Hamlet | Vanarama National League South |
| 25 | Sat 29 Feb 2020 | 10-1 v Tonbridge AngelsDulwich Hamlet 0-1 Tonbridge Angels | Vanarama National League South |
| 26 | Sat 7 Mar 2020 | 11-2 v WealdstoneWealdstone 2-1 Dulwich Hamlet | Vanarama National League South |
| 27 | Sat 14 Mar 2020 | 12-1 v Hemel Hempstead TownDulwich Hamlet 2-1 Hemel Hempstead Town | Vanarama National League South |
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