| 1 | Fri 12 Jul 2019 | 12-1 v ChesterChester 1-2 Dulwich Hamlet | Friendly |
| 2 | Tue 19 Nov 2019 | 12-3 v Wingate & FinchleyDulwich Hamlet 2-3 Wingate & Finchley | London County Cup Second Round |
| 3 | Tue 26 Nov 2019 | 132-1 v Chippenham TownChippenham Town 1-2 Dulwich Hamlet | Buildbase FA Trophy Third Qualifying Round Replay |
| 4 | Sat 30 Nov 2019 | 11-2 v Oxford CityOxford City 2-1 Dulwich Hamlet | Vanarama National League South |
| 5 | Sat 7 Dec 2019 | 11-1 v DartfordDulwich Hamlet 1-1 Dartford | Vanarama National League South |
| 6 | Sat 14 Dec 2019 | 10-1 v HornchurchHornchurch 1-0 Dulwich Hamlet | Buildbase FA Trophy First Round |
| 7 | Sat 21 Dec 2019 | 14-1 v Hungerford TownHungerford Town 1-4 Dulwich Hamlet | Vanarama National League South |
| 8 | Thu 26 Dec 2019 | 11-2 v Hampton & Richmond BoroughDulwich Hamlet 1-2 Hampton & Richmond Borough | Vanarama National League South |
| 9 | Sat 28 Dec 2019 | 11-4 v Maidstone UnitedMaidstone United 4-1 Dulwich Hamlet | Vanarama National League South |
| 10 | Sat 7 Mar 2020 | 10-2 v Carshalton AthleticCarshalton Athletic 2-0 Cheshunt | BetVictor Isthmian Premier Division |
| 11 | Wed 11 Mar 2020 | 1 4-2 v KingstonianKingstonian 2-4 Cheshunt | BetVictor Isthmian Premier Division |
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