| 1 | Tue 9 Jul 2019 | 60-2 v Colchester UnitedDulwich Hamlet 0-2 Colchester United | Friendly |
| 2 | Fri 12 Jul 2019 | 62-1 v ChesterChester 1-2 Dulwich Hamlet | Friendly |
| 3 | Sat 13 Jul 2019 | 174-2 v MarineMarine 2-4 Dulwich Hamlet | Friendly |
| 4 | Tue 16 Jul 2019 | 141-1 v BromleyDulwich Hamlet 1-1 Bromley | Friendly |
| 5 | Tue 23 Jul 2019 | 60-2 v Sutton UnitedSutton United 2-0 Dulwich Hamlet | Friendly |
| 6 | Sat 3 Aug 2019 | 6 2-1 v Tonbridge AngelsTonbridge Angels 1-2 Dulwich Hamlet | Vanarama National League South |
| 7 | Tue 6 Aug 2019 | 61-0 v WealdstoneDulwich Hamlet 1-0 Wealdstone | Vanarama National League South |
| 8 | Tue 13 Aug 2019 | 60-1 v Hemel Hempstead TownHemel Hempstead Town 1-0 Dulwich Hamlet | Vanarama National League South |
| 9 | Sat 17 Aug 2019 | 62-2 v Concord RangersDulwich Hamlet 2-2 Concord Rangers | Vanarama National League South |
| 10 | Sat 24 Aug 2019 | 63-0 v Eastbourne BoroughEastbourne Borough 0-3 Dulwich Hamlet | Vanarama National League South |
| 11 | Mon 26 Aug 2019 | 62-3 v Slough TownDulwich Hamlet 2-3 Slough Town | Vanarama National League South |
| 12 | Sat 7 Sep 2019 | 61-2 v Braintree TownBraintree Town 2-1 Dulwich Hamlet | Vanarama National League South |
| 13 | Sat 14 Sep 2019 | 42-3 v Hungerford TownDulwich Hamlet 2-3 Hungerford Town | Vanarama National League South |
| 14 | Sat 21 Sep 2019 | 86-1 v Bognor Regis TownDulwich Hamlet 6-1 Bognor Regis Town | Emirates FA Cup Second Qualifying Round |
| 15 | Sat 28 Sep 2019 | 8 2-2 v Chippenham TownChippenham Town 2-2 Dulwich Hamlet | Vanarama National League South |
| 16 | Sat 5 Oct 2019 | 83-0 v Eastbourne BoroughDulwich Hamlet 3-0 Eastbourne Borough | Emirates FA Cup Third Qualifying Round |
| 17 | Sat 12 Oct 2019 | 52-2 v WeymouthDulwich Hamlet 2-2 Weymouth | Vanarama National League South |
| 18 | Sat 19 Oct 2019 | 52-1 v Havant & WaterloovilleHavant & Waterlooville 1-2 Dulwich Hamlet | Emirates FA Cup Fourth Qualifying Round |
| 19 | Sat 26 Oct 2019 | 51-1 v Chelmsford CityChelmsford City 1-1 Dulwich Hamlet | Vanarama National League South |
| 20 | Sat 2 Nov 2019 | 51-3 v Bath CityDulwich Hamlet 1-3 Bath City | Vanarama National League South |
| 21 | Tue 19 Nov 2019 | 62-3 v Wingate & FinchleyDulwich Hamlet 2-3 Wingate & Finchley | London County Cup Second Round |
| 22 | Sat 23 Nov 2019 | 22-2 v Chippenham TownDulwich Hamlet 2-2 Chippenham Town | Buildbase FA Trophy Third Qualifying Round |
| 23 | Tue 26 Nov 2019 | 22-1 v Chippenham TownChippenham Town 1-2 Dulwich Hamlet | Buildbase FA Trophy Third Qualifying Round Replay |
| 24 | Sat 30 Nov 2019 | 21-2 v Oxford CityOxford City 2-1 Dulwich Hamlet | Vanarama National League South |
| 25 | Sat 7 Dec 2019 | 51-1 v DartfordDulwich Hamlet 1-1 Dartford | Vanarama National League South |
| 26 | Sat 14 Dec 2019 | 80-1 v HornchurchHornchurch 1-0 Dulwich Hamlet | Buildbase FA Trophy First Round |
| 27 | Sat 21 Dec 2019 | 8 4-1 v Hungerford TownHungerford Town 1-4 Dulwich Hamlet | Vanarama National League South |
| 28 | Thu 26 Dec 2019 | 81-2 v Hampton & Richmond BoroughDulwich Hamlet 1-2 Hampton & Richmond Borough | Vanarama National League South |
| 29 | Sat 28 Dec 2019 | 61-4 v Maidstone UnitedMaidstone United 4-1 Dulwich Hamlet | Vanarama National League South |
| 30 | Wed 1 Jan 2020 | 4 3-0 v Hampton & Richmond BoroughHampton & Richmond Borough 0-3 Dulwich Hamlet | Vanarama National League South |
| 31 | Sat 4 Jan 2020 | 46-0 v Braintree TownDulwich Hamlet 6-0 Braintree Town | Vanarama National League South |
| 32 | Sat 11 Jan 2020 | 4 1-1 v WeymouthWeymouth 1-1 Dulwich Hamlet | Vanarama National League South |
| 33 | Sat 18 Jan 2020 | 41-1 v Chippenham TownDulwich Hamlet 1-1 Chippenham Town | Vanarama National League South |
| 34 | Tue 21 Jan 2020 | 41-3 v Havant & WaterloovilleDulwich Hamlet 1-3 Havant & Waterlooville | Vanarama National League South |
| 35 | Sat 15 Feb 2020 | 80-1 v Welling UnitedDulwich Hamlet 0-1 Welling United | Vanarama National League South |
| 36 | Sat 22 Feb 2020 | 8 2-3 v Bath CityBath City 3-2 Dulwich Hamlet | Vanarama National League South |
| 37 | Sat 29 Feb 2020 | 40-1 v Tonbridge AngelsDulwich Hamlet 0-1 Tonbridge Angels | Vanarama National League South |
| 38 | Sat 7 Mar 2020 | 4 1-2 v WealdstoneWealdstone 2-1 Dulwich Hamlet | Vanarama National League South |
| 39 | Sat 14 Mar 2020 | 42-1 v Hemel Hempstead TownDulwich Hamlet 2-1 Hemel Hempstead Town | Vanarama National League South |
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