| 1 | Fri 12 Jul 2019 | 162-1 v ChesterChester 1-2 Dulwich Hamlet | Friendly |
| 2 | Sat 13 Jul 2019 | 64-2 v MarineMarine 2-4 Dulwich Hamlet | Friendly |
| 3 | Tue 16 Jul 2019 | 61-1 v BromleyDulwich Hamlet 1-1 Bromley | Friendly |
| 4 | Tue 23 Jul 2019 | 50-2 v Sutton UnitedSutton United 2-0 Dulwich Hamlet | Friendly |
| 5 | Sat 3 Aug 2019 | 152-1 v Tonbridge AngelsTonbridge Angels 1-2 Dulwich Hamlet | Vanarama National League South |
| 6 | Tue 6 Aug 2019 | 151-0 v WealdstoneDulwich Hamlet 1-0 Wealdstone | Vanarama National League South |
| 7 | Sat 10 Aug 2019 | 62-1 v St Albans CityDulwich Hamlet 2-1 St Albans City | Vanarama National League South |
| 8 | Sat 24 Aug 2019 | 153-0 v Eastbourne BoroughEastbourne Borough 0-3 Dulwich Hamlet | Vanarama National League South |
| 9 | Mon 26 Aug 2019 | 52-3 v Slough TownDulwich Hamlet 2-3 Slough Town | Vanarama National League South |
| 10 | Sat 31 Aug 2019 | 20-0 v Dorking WanderersDorking Wanderers 0-0 Dulwich Hamlet | Vanarama National League South |
| 11 | Tue 3 Sep 2019 | 60-1 v Maidstone UnitedDulwich Hamlet 0-1 Maidstone United | Vanarama National League South |
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