| 1 | Tue 16 Jul 2019 | 151-1 v BromleyDulwich Hamlet 1-1 Bromley | Friendly |
| 2 | Tue 23 Jul 2019 | 70-2 v Sutton UnitedSutton United 2-0 Dulwich Hamlet | Friendly |
| 3 | Sat 3 Aug 2019 | 112-1 v Tonbridge AngelsTonbridge Angels 1-2 Dulwich Hamlet | Vanarama National League South |
| 4 | Tue 6 Aug 2019 | 111-0 v WealdstoneDulwich Hamlet 1-0 Wealdstone | Vanarama National League South |
| 5 | Sat 10 Aug 2019 | 112-1 v St Albans CityDulwich Hamlet 2-1 St Albans City | Vanarama National League South |
| 6 | Tue 13 Aug 2019 | 110-1 v Hemel Hempstead TownHemel Hempstead Town 1-0 Dulwich Hamlet | Vanarama National League South |
| 7 | Sat 17 Aug 2019 | 112-2 v Concord RangersDulwich Hamlet 2-2 Concord Rangers | Vanarama National League South |
| 8 | Mon 26 Aug 2019 | 72-3 v Slough TownDulwich Hamlet 2-3 Slough Town | Vanarama National League South |
| 9 | Sat 31 Aug 2019 | 160-0 v Dorking WanderersDorking Wanderers 0-0 Dulwich Hamlet | Vanarama National League South |
| 10 | Tue 3 Sep 2019 | 120-1 v Maidstone UnitedDulwich Hamlet 0-1 Maidstone United | Vanarama National League South |
| 11 | Sat 14 Sep 2019 | 7 2-3 v Hungerford TownDulwich Hamlet 2-3 Hungerford Town | Vanarama National League South |
| 12 | Sat 21 Sep 2019 | 116-1 v Bognor Regis TownDulwich Hamlet 6-1 Bognor Regis Town | Emirates FA Cup Second Qualifying Round |
| 13 | Sat 28 Sep 2019 | 112-2 v Chippenham TownChippenham Town 2-2 Dulwich Hamlet | Vanarama National League South |
| 14 | Fri 8 Nov 2019 | 111-4 v Carlisle UnitedDulwich Hamlet 1-4 Carlisle United | Emirates FA Cup First Round |
| 15 | Tue 12 Nov 2019 | 110-0 v Welling UnitedWelling United 0-0 Dulwich Hamlet | Vanarama National League South |
| 16 | Sat 16 Nov 2019 | 170-1 v Billericay TownDulwich Hamlet 0-1 Billericay Town | Vanarama National League South |
| 17 | Tue 19 Nov 2019 | 122-3 v Wingate & FinchleyDulwich Hamlet 2-3 Wingate & Finchley | London County Cup Second Round |
| 18 | Sat 30 Nov 2019 | 171-2 v Oxford CityOxford City 2-1 Dulwich Hamlet | Vanarama National League South |
| 19 | Thu 26 Dec 2019 | 161-2 v Hampton & Richmond BoroughDulwich Hamlet 1-2 Hampton & Richmond Borough | Vanarama National League South |
| 20 | Sat 28 Dec 2019 | 71-4 v Maidstone UnitedMaidstone United 4-1 Dulwich Hamlet | Vanarama National League South |
| 21 | Wed 1 Jan 2020 | 73-0 v Hampton & Richmond BoroughHampton & Richmond Borough 0-3 Dulwich Hamlet | Vanarama National League South |
| 22 | Sat 4 Jan 2020 | 76-0 v Braintree TownDulwich Hamlet 6-0 Braintree Town | Vanarama National League South |
| 23 | Sat 11 Jan 2020 | 71-1 v WeymouthWeymouth 1-1 Dulwich Hamlet | Vanarama National League South |
| 24 | Sat 18 Jan 2020 | 71-1 v Chippenham TownDulwich Hamlet 1-1 Chippenham Town | Vanarama National League South |
| 25 | Tue 21 Jan 2020 | 71-3 v Havant & WaterloovilleDulwich Hamlet 1-3 Havant & Waterlooville | Vanarama National League South |
| 26 | Sat 25 Jan 2020 | 110-1 v DartfordDartford 1-0 Dulwich Hamlet | Vanarama National League South |
| 27 | Sat 1 Feb 2020 | 115-3 v Chelmsford CityDulwich Hamlet 5-3 Chelmsford City | Vanarama National League South |
| 28 | Sat 8 Feb 2020 | 70-0 v Havant & WaterloovilleHavant & Waterlooville 0-0 Dulwich Hamlet | Vanarama National League South |
| 29 | Sat 15 Feb 2020 | 110-1 v Welling UnitedDulwich Hamlet 0-1 Welling United | Vanarama National League South |
| 30 | Sat 22 Feb 2020 | 72-3 v Bath CityBath City 3-2 Dulwich Hamlet | Vanarama National League South |
| 31 | Sat 29 Feb 2020 | 70-1 v Tonbridge AngelsDulwich Hamlet 0-1 Tonbridge Angels | Vanarama National League South |
| 32 | Sat 7 Mar 2020 | 7 1-2 v WealdstoneWealdstone 2-1 Dulwich Hamlet | Vanarama National League South |
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