| 1 | Fri 8 Nov 2019 | 41-4 v Carlisle UnitedDulwich Hamlet 1-4 Carlisle United | Emirates FA Cup First Round |
| 2 | Tue 12 Nov 2019 | 40-0 v Welling UnitedWelling United 0-0 Dulwich Hamlet | Vanarama National League South |
| 3 | Sat 16 Nov 2019 | 80-1 v Billericay TownDulwich Hamlet 0-1 Billericay Town | Vanarama National League South |
| 4 | Tue 19 Nov 2019 | 142-3 v Wingate & FinchleyDulwich Hamlet 2-3 Wingate & Finchley | London County Cup Second Round |
| 5 | Sat 23 Nov 2019 | 42-2 v Chippenham TownDulwich Hamlet 2-2 Chippenham Town | Buildbase FA Trophy Third Qualifying Round |
| 6 | Tue 26 Nov 2019 | 8 2-1 v Chippenham TownChippenham Town 1-2 Dulwich Hamlet | Buildbase FA Trophy Third Qualifying Round Replay |
| 7 | Sat 30 Nov 2019 | 8 1-2 v Oxford CityOxford City 2-1 Dulwich Hamlet | Vanarama National League South |
| 8 | Sat 7 Dec 2019 | 81-1 v DartfordDulwich Hamlet 1-1 Dartford | Vanarama National League South |
| 9 | Mon 30 Dec 2019 | 1-2 v Derby CountyDerby County 2-1 Charlton Athletic | Sky Bet Championship |
| 10 | Thu 2 Jan 2020 | 0-1 v Swansea CitySwansea City 1-0 Charlton Athletic | Sky Bet Championship |
| 11 | Sat 11 Jan 2020 | 2-2 v West Bromwich AlbionCharlton Athletic 2-2 West Bromwich Albion | Sky Bet Championship |
| 12 | Sat 18 Jan 2020 | 1-2 v Preston North EndPreston North End 2-1 Charlton Athletic | Sky Bet Championship |
| 13 | Sat 15 Feb 2020 | 1-1 v Notts CountyNotts County 1-1 Woking | Vanarama National League |
| 14 | Sat 22 Feb 2020 | 1-1 v Stockport CountyWoking 1-1 Stockport County | Vanarama National League |
| 15 | Sat 29 Feb 2020 | 2-0 v Maidenhead UnitedWoking 2-0 Maidenhead United | Vanarama National League |
| 16 | Sat 7 Mar 2020 | 2-0 v FC Halifax TownFC Halifax Town 0-2 Woking | Vanarama National League |
| 17 | Tue 10 Mar 2020 | 1-3 v BarnetWoking 1-3 Barnet | Vanarama National League |
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