| 1 | Sat 7 Sep 2019 | 71-2 v Braintree TownBraintree Town 2-1 Dulwich Hamlet | Vanarama National League South |
| 2 | Sat 14 Sep 2019 | 102-3 v Hungerford TownDulwich Hamlet 2-3 Hungerford Town | Vanarama National League South |
| 3 | Sat 5 Oct 2019 | 113-0 v Eastbourne BoroughDulwich Hamlet 3-0 Eastbourne Borough | Emirates FA Cup Third Qualifying Round |
| 4 | Sat 12 Oct 2019 | 112-2 v WeymouthDulwich Hamlet 2-2 Weymouth | Vanarama National League South |
| 5 | Sat 19 Oct 2019 | 112-1 v Havant & WaterloovilleHavant & Waterlooville 1-2 Dulwich Hamlet | Emirates FA Cup Fourth Qualifying Round |
| 6 | Sat 26 Oct 2019 | 111-1 v Chelmsford CityChelmsford City 1-1 Dulwich Hamlet | Vanarama National League South |
| 7 | Sat 2 Nov 2019 | 111-3 v Bath CityDulwich Hamlet 1-3 Bath City | Vanarama National League South |
| 8 | Sat 16 Nov 2019 | 150-1 v Billericay TownDulwich Hamlet 0-1 Billericay Town | Vanarama National League South |
| 9 | Tue 19 Nov 2019 | 92-3 v Wingate & FinchleyDulwich Hamlet 2-3 Wingate & Finchley | London County Cup Second Round |
| 10 | Sat 30 Nov 2019 | 161-2 v Oxford CityOxford City 2-1 Dulwich Hamlet | Vanarama National League South |
| 11 | Sat 28 Dec 2019 | 171-4 v Maidstone UnitedMaidstone United 4-1 Dulwich Hamlet | Vanarama National League South |
| 12 | Wed 1 Jan 2020 | 143-0 v Hampton & Richmond BoroughHampton & Richmond Borough 0-3 Dulwich Hamlet | Vanarama National League South |
| 13 | Tue 21 Jan 2020 | 151-3 v Havant & WaterloovilleDulwich Hamlet 1-3 Havant & Waterlooville | Vanarama National League South |
| 14 | Sat 25 Jan 2020 | 170-1 v DartfordDartford 1-0 Dulwich Hamlet | Vanarama National League South |
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