| 1 | Fri 12 Jul 2019 | 142-1 v ChesterChester 1-2 Dulwich Hamlet | Friendly |
| 2 | Sat 10 Aug 2019 | 10 2-1 v St Albans CityDulwich Hamlet 2-1 St Albans City | Vanarama National League South |
| 3 | Tue 13 Aug 2019 | 170-1 v Hemel Hempstead TownHemel Hempstead Town 1-0 Dulwich Hamlet | Vanarama National League South |
| 4 | Sat 31 Aug 2019 | 100-0 v Dorking WanderersDorking Wanderers 0-0 Dulwich Hamlet | Vanarama National League South |
| 5 | Tue 3 Sep 2019 | 110-1 v Maidstone UnitedDulwich Hamlet 0-1 Maidstone United | Vanarama National League South |
| 6 | Sat 7 Sep 2019 | 141-2 v Braintree TownBraintree Town 2-1 Dulwich Hamlet | Vanarama National League South |
| 7 | Sat 21 Sep 2019 | 146-1 v Bognor Regis TownDulwich Hamlet 6-1 Bognor Regis Town | Emirates FA Cup Second Qualifying Round |
| 8 | Sat 28 Sep 2019 | 102-2 v Chippenham TownChippenham Town 2-2 Dulwich Hamlet | Vanarama National League South |
| 9 | Sat 12 Oct 2019 | 82-2 v WeymouthDulwich Hamlet 2-2 Weymouth | Vanarama National League South |
| 10 | Sat 19 Oct 2019 | 82-1 v Havant & WaterloovilleHavant & Waterlooville 1-2 Dulwich Hamlet | Emirates FA Cup Fourth Qualifying Round |
| 11 | Sat 26 Oct 2019 | 81-1 v Chelmsford CityChelmsford City 1-1 Dulwich Hamlet | Vanarama National League South |
| 12 | Sat 2 Nov 2019 | 81-3 v Bath CityDulwich Hamlet 1-3 Bath City | Vanarama National League South |
| 13 | Fri 8 Nov 2019 | 81-4 v Carlisle UnitedDulwich Hamlet 1-4 Carlisle United | Emirates FA Cup First Round |
| 14 | Tue 12 Nov 2019 | 80-0 v Welling UnitedWelling United 0-0 Dulwich Hamlet | Vanarama National League South |
| 15 | Sat 16 Nov 2019 | 100-1 v Billericay TownDulwich Hamlet 0-1 Billericay Town | Vanarama National League South |
| 16 | Sat 23 Nov 2019 | 82-2 v Chippenham TownDulwich Hamlet 2-2 Chippenham Town | Buildbase FA Trophy Third Qualifying Round |
| 17 | Tue 26 Nov 2019 | 102-1 v Chippenham TownChippenham Town 1-2 Dulwich Hamlet | Buildbase FA Trophy Third Qualifying Round Replay |
| 18 | Sat 30 Nov 2019 | 101-2 v Oxford CityOxford City 2-1 Dulwich Hamlet | Vanarama National League South |
| 19 | Sat 7 Dec 2019 | 101-1 v DartfordDulwich Hamlet 1-1 Dartford | Vanarama National League South |
| 20 | Sat 14 Dec 2019 | 170-1 v HornchurchHornchurch 1-0 Dulwich Hamlet | Buildbase FA Trophy First Round |
| 21 | Sat 21 Dec 2019 | 104-1 v Hungerford TownHungerford Town 1-4 Dulwich Hamlet | Vanarama National League South |
| 22 | Thu 26 Dec 2019 | 101-2 v Hampton & Richmond BoroughDulwich Hamlet 1-2 Hampton & Richmond Borough | Vanarama National League South |
| 23 | Sat 28 Dec 2019 | 101-4 v Maidstone UnitedMaidstone United 4-1 Dulwich Hamlet | Vanarama National League South |
| 24 | Wed 1 Jan 2020 | 8 3-0 v Hampton & Richmond BoroughHampton & Richmond Borough 0-3 Dulwich Hamlet | Vanarama National League South |
| 25 | Sat 4 Jan 2020 | 86-0 v Braintree TownDulwich Hamlet 6-0 Braintree Town | Vanarama National League South |
| 26 | Sat 11 Jan 2020 | 81-1 v WeymouthWeymouth 1-1 Dulwich Hamlet | Vanarama National League South |
| 27 | Sat 18 Jan 2020 | 81-1 v Chippenham TownDulwich Hamlet 1-1 Chippenham Town | Vanarama National League South |
| 28 | Tue 21 Jan 2020 | 161-3 v Havant & WaterloovilleDulwich Hamlet 1-3 Havant & Waterlooville | Vanarama National League South |
| 29 | Sat 25 Jan 2020 | 80-1 v DartfordDartford 1-0 Dulwich Hamlet | Vanarama National League South |
| 30 | Sat 8 Feb 2020 | 140-0 v Havant & WaterloovilleHavant & Waterlooville 0-0 Dulwich Hamlet | Vanarama National League South |
| 31 | Sat 22 Feb 2020 | 102-3 v Bath CityBath City 3-2 Dulwich Hamlet | Vanarama National League South |
| 32 | Sat 14 Mar 2020 | 102-1 v Hemel Hempstead TownDulwich Hamlet 2-1 Hemel Hempstead Town | Vanarama National League South |
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