| 1 | Tue 11 Jul 2023 | 12-2 v BromleyDulwich Hamlet 2-2 Bromley | Friendly |
| 2 | Sat 15 Jul 2023 | 10-0 v AveleyAveley 0-0 Dulwich Hamlet | Friendly |
| 3 | Tue 18 Jul 2023 | 13-1 v Welling UnitedWelling United 1-3 Dulwich Hamlet | Friendly |
| 4 | Tue 25 Jul 2023 | 11-1 v Tooting & Mitcham UnitedTooting & Mitcham United 1-1 Dulwich Hamlet | Friendly |
| 5 | Fri 28 Jul 2023 | 13-1 v MillwallDulwich Hamlet 3-1 Millwall | Friendly |
| 6 | Tue 1 Aug 2023 | 12-2 v Welwyn Garden CityWelwyn Garden City 2-2 Dulwich Hamlet | Friendly |
| 7 | Sat 5 Aug 2023 | 13-2 v Cray Valley PMCray Valley PM 2-3 Dulwich Hamlet | Friendly |
| 8 | Sat 12 Aug 2023 | 1 2-2 v Hashtag UnitedHashtag United 2-2 Dulwich Hamlet | Isthmian League - Premier Division |
| 9 | Tue 15 Aug 2023 | 14-1 v Canvey IslandDulwich Hamlet 4-1 Canvey Island | Isthmian League - Premier Division |
| 10 | Sat 19 Aug 2023 | 11-2 v Hastings UnitedDulwich Hamlet 1-2 Hastings United | Isthmian League - Premier Division |
| 11 | Sat 26 Aug 2023 | 12-3 v HorshamHorsham 3-2 Dulwich Hamlet | Isthmian League - Premier Division |
| 12 | Mon 28 Aug 2023 | 12-5 v Chatham TownDulwich Hamlet 2-5 Chatham Town | Isthmian League - Premier Division |
| 13 | Sat 2 Sep 2023 | 11-1 v Haringey BoroughDulwich Hamlet 1-1 Haringey Borough | Emirates FA Cup First Qualifying Round |
| 14 | Tue 5 Sep 2023 | 11-2 v Haringey BoroughHaringey Borough 2-1 Dulwich Hamlet | Emirates FA Cup First Qualifying Round Replay |
| 15 | Tue 19 Sep 2023 | 12-0 v Erith TownErith Town 0-2 Dulwich Hamlet | London County Cup First Round |
| 16 | Sat 23 Sep 2023 | 12-0 v Concord RangersDulwich Hamlet 2-0 Concord Rangers | Isthmian League - Premier Division |
| 17 | Tue 26 Sep 2023 | 1 1-2 v HornchurchHornchurch 2-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 18 | Sat 30 Sep 2023 | 11-2 v CheshuntCheshunt 2-1 Dulwich Hamlet | Isthmian League - Premier Division |
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