| 1 | Wed 11 Oct 2023 | 12-2 v Gosport BoroughGosport Borough 2-2 Dorchester Town | Southern League - Premier South |
| 2 | Sat 21 Oct 2023 | 10-1 v HendonHendon 1-0 Dorchester Town | Southern League - Premier South |
| 3 | Tue 24 Oct 2023 | 11-2 v SholingDorchester Town 1-2 Sholing | Southern League - Premier South |
| 4 | Sat 28 Oct 2023 | 11-1 v Hayes & Yeading UnitedDorchester Town 1-1 Hayes & Yeading United | Southern League - Premier South |
| 5 | Sat 11 Nov 2023 | 14-1 v Basingstoke TownDorchester Town 4-1 Basingstoke Town | Southern League - Premier South |
| 6 | Tue 14 Nov 2023 | 11-2 v Bracknell TownDorchester Town 1-2 Bracknell Town | Southern League - Premier South |
| 7 | Sat 25 Nov 2023 | 12-3 v SalisburySalisbury 3-2 Dorchester Town | Southern League - Premier South |
| 8 | Sat 9 Dec 2023 | 12-1 v Swindon SupermarineSwindon Supermarine 1-2 Dorchester Town | Southern League - Premier South |
| 9 | Sat 16 Dec 2023 | 11-2 v Walton & HershamDorchester Town 1-2 Walton & Hersham | Southern League - Premier South |
| 10 | Sat 23 Dec 2023 | 10-2 v Chesham UnitedChesham United 2-0 Dorchester Town | Southern League - Premier South |
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