| 1 | Sat 15 Jul 2023 | 340-0 v AveleyAveley 0-0 Dulwich Hamlet | Friendly |
| 2 | Tue 18 Jul 2023 | 403-1 v Welling UnitedWelling United 1-3 Dulwich Hamlet | Friendly |
| 3 | Sat 22 Jul 2023 | 42-1 v Erith & BelvedereDulwich Hamlet 2-1 Erith & Belvedere | Friendly |
| 4 | Tue 25 Jul 2023 | 201-1 v Tooting & Mitcham UnitedTooting & Mitcham United 1-1 Dulwich Hamlet | Friendly |
| 5 | Tue 1 Aug 2023 | 22-2 v Welwyn Garden CityWelwyn Garden City 2-2 Dulwich Hamlet | Friendly |
| 6 | Tue 19 Sep 2023 | 2 2-0 v Erith TownErith Town 0-2 Dulwich Hamlet | London County Cup First Round |
| 7 | Sat 23 Sep 2023 | 22-0 v Concord RangersDulwich Hamlet 2-0 Concord Rangers | Isthmian League - Premier Division |
| 8 | Tue 26 Sep 2023 | 21-2 v HornchurchHornchurch 2-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 9 | Sat 4 Nov 2023 | 121-1 v Haringey BoroughHaringey Borough 1-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 10 | Tue 7 Nov 2023 | 22-3 v KingstonianKingstonian 3-2 Dulwich Hamlet | Velocity Cup Third Round |
| 11 | Sat 11 Nov 2023 | 22-2 v MargateDulwich Hamlet 2-2 Margate | Isthmian League - Premier Division |
| 12 | Sat 18 Nov 2023 | 23-1 v Folkestone InvictaDulwich Hamlet 3-1 Folkestone Invicta | Isthmian League - Premier Division |
| 13 | Sat 25 Nov 2023 | 21-1 v Cray WanderersCray Wanderers 1-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 14 | Tue 28 Nov 2023 | 22-2 v Potters Bar TownDulwich Hamlet 2-2 Potters Bar Town | Isthmian League - Premier Division |
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