| 1 | Sat 28 Sep | 11-4 v Bowers & PitseaBowers & Pitsea 4-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 2 | Tue 1 Oct | 10-0 v Chichester CityChichester City 0-0 Dulwich Hamlet | Isthmian League - Premier Division |
| 3 | Sat 5 Oct | 11-0 v DartfordDartford 0-1 Dulwich Hamlet | Isuzu FA Trophy Third Qualifying Round |
| 4 | Sat 12 Oct | 13-0 v Hastings UnitedDulwich Hamlet 3-0 Hastings United | Isthmian League - Premier Division |
| 5 | Sat 19 Oct | 10-1 v Billericay TownDulwich Hamlet 0-1 Billericay Town | Isthmian League - Premier Division |
| 6 | Sat 26 Oct | 11-1 v Hashtag UnitedDulwich Hamlet 1-1 Hashtag United | Isuzu FA Trophy First Round |
| 7 | Sat 2 Nov | 12-1 v Wingate & FinchleyDulwich Hamlet 2-1 Wingate & Finchley | Isthmian League - Premier Division |
| 8 | Tue 5 Nov | 10-3 v HendonHendon 3-0 Dulwich Hamlet | Isthmian League - Premier Division |
| 9 | Sat 9 Nov | 13-1 v Potters Bar TownDulwich Hamlet 3-1 Potters Bar Town | Isthmian League - Premier Division |
| 10 | Tue 19 Nov | 11-2 v Folkestone InvictaFolkestone Invicta 2-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 11 | Sat 23 Nov | 10-2 v Hashtag UnitedDulwich Hamlet 0-2 Hashtag United | Isthmian League - Premier Division |
| 12 | Sat 30 Nov | 11-1 v CheshuntCheshunt 1-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 13 | Sat 7 Dec | 11-4 v Dover AthleticDulwich Hamlet 1-4 Dover Athletic | Isthmian League - Premier Division |
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