| 1 | Tue 18 Jul 2023 | 173-1 v Welling UnitedWelling United 1-3 Dulwich Hamlet | Friendly |
| 2 | Sat 22 Jul 2023 | 40 2-1 v Erith & BelvedereDulwich Hamlet 2-1 Erith & Belvedere | Friendly |
| 3 | Sat 5 Aug 2023 | 23-2 v Cray Valley PMCray Valley PM 2-3 Dulwich Hamlet | Friendly |
| 4 | Tue 15 Aug 2023 | 17 4-1 v Canvey IslandDulwich Hamlet 4-1 Canvey Island | Isthmian League - Premier Division |
| 5 | Sat 19 Aug 2023 | 17 1-2 v Hastings UnitedDulwich Hamlet 1-2 Hastings United | Isthmian League - Premier Division |
| 6 | Sat 26 Aug 2023 | 172-3 v HorshamHorsham 3-2 Dulwich Hamlet | Isthmian League - Premier Division |
| 7 | Mon 28 Aug 2023 | 122-5 v Chatham TownDulwich Hamlet 2-5 Chatham Town | Isthmian League - Premier Division |
| 8 | Sat 2 Sep 2023 | 121-1 v Haringey BoroughDulwich Hamlet 1-1 Haringey Borough | Emirates FA Cup First Qualifying Round |
| 9 | Sat 30 Sep 2023 | 21-2 v CheshuntCheshunt 2-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 10 | Sat 7 Oct 2023 | 21-0 v CheshuntCheshunt 0-1 Dulwich Hamlet | Isuzu FA Trophy Third Qualifying Round |
| 11 | Tue 10 Oct 2023 | 20-3 v Billericay TownBillericay Town 3-0 Dulwich Hamlet | Isthmian League - Premier Division |
| 12 | Sat 14 Oct 2023 | 23-2 v KingstonianDulwich Hamlet 3-2 Kingstonian | Isthmian League - Premier Division |
| 13 | Sat 21 Oct 2023 | 21-1 v WhitehawkWhitehawk 1-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 14 | Tue 24 Oct 2023 | 2 3-2 v Wingate & FinchleyWingate & Finchley 2-3 Dulwich Hamlet | Isthmian League - Premier Division |
| 15 | Sat 28 Oct 2023 | 20-2 v LewesDulwich Hamlet 0-2 Lewes | Isuzu FA Trophy First Round |
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