| 1 | Tue 9 Jul 2019 | 110-2 v Colchester UnitedDulwich Hamlet 0-2 Colchester United | Friendly |
| 2 | Fri 12 Jul 2019 | 122-1 v ChesterChester 1-2 Dulwich Hamlet | Friendly |
| 3 | Sat 13 Jul 2019 | 104-2 v MarineMarine 2-4 Dulwich Hamlet | Friendly |
| 4 | Tue 16 Jul 2019 | 101-1 v BromleyDulwich Hamlet 1-1 Bromley | Friendly |
| 5 | Tue 23 Jul 2019 | 90-2 v Sutton UnitedSutton United 2-0 Dulwich Hamlet | Friendly |
| 6 | Sat 3 Aug 2019 | 122-1 v Tonbridge AngelsTonbridge Angels 1-2 Dulwich Hamlet | Vanarama National League South |
| 7 | Tue 6 Aug 2019 | 121-0 v WealdstoneDulwich Hamlet 1-0 Wealdstone | Vanarama National League South |
| 8 | Sat 17 Aug 2019 | 122-2 v Concord RangersDulwich Hamlet 2-2 Concord Rangers | Vanarama National League South |
| 9 | Sat 21 Sep 2019 | 166-1 v Bognor Regis TownDulwich Hamlet 6-1 Bognor Regis Town | Emirates FA Cup Second Qualifying Round |
| 10 | Sat 28 Sep 2019 | 162-2 v Chippenham TownChippenham Town 2-2 Dulwich Hamlet | Vanarama National League South |
| 11 | Sat 5 Oct 2019 | 10 3-0 v Eastbourne BoroughDulwich Hamlet 3-0 Eastbourne Borough | Emirates FA Cup Third Qualifying Round |
| 12 | Sat 12 Oct 2019 | 102-2 v WeymouthDulwich Hamlet 2-2 Weymouth | Vanarama National League South |
| 13 | Sat 19 Oct 2019 | 102-1 v Havant & WaterloovilleHavant & Waterlooville 1-2 Dulwich Hamlet | Emirates FA Cup Fourth Qualifying Round |
| 14 | Sat 26 Oct 2019 | 101-1 v Chelmsford CityChelmsford City 1-1 Dulwich Hamlet | Vanarama National League South |
| 15 | Sat 2 Nov 2019 | 101-3 v Bath CityDulwich Hamlet 1-3 Bath City | Vanarama National League South |
| 16 | Fri 8 Nov 2019 | 101-4 v Carlisle UnitedDulwich Hamlet 1-4 Carlisle United | Emirates FA Cup First Round |
| 17 | Tue 12 Nov 2019 | 100-0 v Welling UnitedWelling United 0-0 Dulwich Hamlet | Vanarama National League South |
| 18 | Sat 23 Nov 2019 | 162-2 v Chippenham TownDulwich Hamlet 2-2 Chippenham Town | Buildbase FA Trophy Third Qualifying Round |
| 19 | Sat 30 Nov 2019 | 141-2 v Oxford CityOxford City 2-1 Dulwich Hamlet | Vanarama National League South |
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