| 1 | Tue 9 Jul 2019 | 100-2 v Colchester UnitedDulwich Hamlet 0-2 Colchester United | Friendly |
| 2 | Fri 12 Jul 2019 | 102-1 v ChesterChester 1-2 Dulwich Hamlet | Friendly |
| 3 | Sat 13 Jul 2019 | 114-2 v MarineMarine 2-4 Dulwich Hamlet | Friendly |
| 4 | Tue 16 Jul 2019 | 121-1 v BromleyDulwich Hamlet 1-1 Bromley | Friendly |
| 5 | Tue 23 Jul 2019 | 100-2 v Sutton UnitedSutton United 2-0 Dulwich Hamlet | Friendly |
| 6 | Sat 3 Aug 2019 | 102-1 v Tonbridge AngelsTonbridge Angels 1-2 Dulwich Hamlet | Vanarama National League South |
| 7 | Tue 6 Aug 2019 | 41-0 v WealdstoneDulwich Hamlet 1-0 Wealdstone | Vanarama National League South |
| 8 | Sat 10 Aug 2019 | 82-1 v St Albans CityDulwich Hamlet 2-1 St Albans City | Vanarama National League South |
| 9 | Tue 13 Aug 2019 | 80-1 v Hemel Hempstead TownHemel Hempstead Town 1-0 Dulwich Hamlet | Vanarama National League South |
| 10 | Sat 17 Aug 2019 | 102-2 v Concord RangersDulwich Hamlet 2-2 Concord Rangers | Vanarama National League South |
| 11 | Sat 24 Aug 2019 | 103-0 v Eastbourne BoroughEastbourne Borough 0-3 Dulwich Hamlet | Vanarama National League South |
| 12 | Mon 26 Aug 2019 | 112-3 v Slough TownDulwich Hamlet 2-3 Slough Town | Vanarama National League South |
| 13 | Tue 3 Sep 2019 | 170-1 v Maidstone UnitedDulwich Hamlet 0-1 Maidstone United | Vanarama National League South |
| 14 | Sat 7 Sep 2019 | 111-2 v Braintree TownBraintree Town 2-1 Dulwich Hamlet | Vanarama National League South |
| 15 | Sat 21 Sep 2019 | 106-1 v Bognor Regis TownDulwich Hamlet 6-1 Bognor Regis Town | Emirates FA Cup Second Qualifying Round |
| 16 | Sat 19 Oct 2019 | 152-1 v Havant & WaterloovilleHavant & Waterlooville 1-2 Dulwich Hamlet | Emirates FA Cup Fourth Qualifying Round |
| 17 | Sat 1 Feb 2020 | 105-3 v Chelmsford CityDulwich Hamlet 5-3 Chelmsford City | Vanarama National League South |
| 18 | Sat 8 Feb 2020 | 10 0-0 v Havant & WaterloovilleHavant & Waterlooville 0-0 Dulwich Hamlet | Vanarama National League South |
| 19 | Sat 29 Feb 2020 | 100-1 v Tonbridge AngelsDulwich Hamlet 0-1 Tonbridge Angels | Vanarama National League South |
| 20 | Sat 7 Mar 2020 | 141-2 v WealdstoneWealdstone 2-1 Dulwich Hamlet | Vanarama National League South |
| 21 | Sat 14 Mar 2020 | 142-1 v Hemel Hempstead TownDulwich Hamlet 2-1 Hemel Hempstead Town | Vanarama National League South |
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