| 1 | Tue 4 Jul 2023 | 53-1 v BashleyDorchester Town 3-1 Bashley | Friendly |
| 2 | Sat 8 Jul 2023 | 60-1 v Weston-super-MareDorchester Town 0-1 Weston-super-Mare | Friendly |
| 3 | Tue 11 Jul 2023 | 62-0 v Portland UnitedPortland United 0-2 Dorchester Town | Friendly |
| 4 | Tue 18 Jul 2023 | 60-5 v Yeovil TownDorchester Town 0-5 Yeovil Town | Friendly |
| 5 | Sat 22 Jul 2023 | 31-2 v Wimborne TownDorchester Town 1-2 Wimborne Town | Friendly |
| 6 | Tue 25 Jul 2023 | 33-0 v EastleighDorchester Town 3-0 Eastleigh | Friendly |
| 7 | Sat 5 Aug 2023 | 32-3 v Merthyr TownMerthyr Town 3-2 Dorchester Town | Southern League - Premier South |
| 8 | Sat 12 Aug 2023 | 42-2 v Harrow BoroughDorchester Town 2-2 Harrow Borough | Southern League - Premier South |
| 9 | Tue 15 Aug 2023 | 40-4 v Winchester CityDorchester Town 0-4 Winchester City | Southern League - Premier South |
| 10 | Sat 19 Aug 2023 | 63-6 v Walton & HershamWalton & Hersham 6-3 Dorchester Town | Southern League - Premier South |
| 11 | Sat 26 Aug 2023 | 30-2 v Chesham UnitedDorchester Town 0-2 Chesham United | Southern League - Premier South |
| 12 | Sat 9 Sep 2023 | 62-1 v Swindon SupermarineDorchester Town 2-1 Swindon Supermarine | Southern League - Premier South |
| 13 | Tue 26 Sep 2023 | 40-5 v Plymouth ParkwayPlymouth Parkway 5-0 Dorchester Town | Southern League - Premier South |
| 14 | Sat 7 Oct 2023 | 151-3 v Merthyr TownMerthyr Town 3-1 Dorchester Town | Isuzu FA Trophy Third Qualifying Round |
| 15 | Wed 11 Oct 2023 | 162-2 v Gosport BoroughGosport Borough 2-2 Dorchester Town | Southern League - Premier South |
| 16 | Sat 21 Oct 2023 | 40-1 v HendonHendon 1-0 Dorchester Town | Southern League - Premier South |
| 17 | Tue 24 Oct 2023 | 141-2 v SholingDorchester Town 1-2 Sholing | Southern League - Premier South |
| 18 | Sat 28 Oct 2023 | 41-1 v Hayes & Yeading UnitedDorchester Town 1-1 Hayes & Yeading United | Southern League - Premier South |
| 19 | Sat 11 Nov 2023 | 44-1 v Basingstoke TownDorchester Town 4-1 Basingstoke Town | Southern League - Premier South |
| 20 | Tue 14 Nov 2023 | 41-2 v Bracknell TownDorchester Town 1-2 Bracknell Town | Southern League - Premier South |
| 21 | Sat 25 Nov 2023 | 152-3 v SalisburySalisbury 3-2 Dorchester Town | Southern League - Premier South |
| 22 | Sat 23 Dec 2023 | 150-2 v Chesham UnitedChesham United 2-0 Dorchester Town | Southern League - Premier South |
| 23 | Tue 26 Dec 2023 | 151-2 v Poole TownDorchester Town 1-2 Poole Town | Southern League - Premier South |
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