| 1 | Tue 4 Jul 2023 | 13-1 v BashleyDorchester Town 3-1 Bashley | Friendly |
| 2 | Sat 8 Jul 2023 | 10-1 v Weston-super-MareDorchester Town 0-1 Weston-super-Mare | Friendly |
| 3 | Tue 11 Jul 2023 | 12-0 v Portland UnitedPortland United 0-2 Dorchester Town | Friendly |
| 4 | Sat 15 Jul 2023 | 11-1 v Frome TownDorchester Town 1-1 Frome Town | Friendly |
| 5 | Tue 18 Jul 2023 | 10-5 v Yeovil TownDorchester Town 0-5 Yeovil Town | Friendly |
| 6 | Sat 22 Jul 2023 | 11-2 v Wimborne TownDorchester Town 1-2 Wimborne Town | Friendly |
| 7 | Tue 25 Jul 2023 | 13-0 v EastleighDorchester Town 3-0 Eastleigh | Friendly |
| 8 | Sat 5 Aug 2023 | 12-3 v Merthyr TownMerthyr Town 3-2 Dorchester Town | Southern League - Premier South |
| 9 | Sat 12 Aug 2023 | 12-2 v Harrow BoroughDorchester Town 2-2 Harrow Borough | Southern League - Premier South |
| 10 | Tue 15 Aug 2023 | 10-4 v Winchester CityDorchester Town 0-4 Winchester City | Southern League - Premier South |
| 11 | Sat 19 Aug 2023 | 13-6 v Walton & HershamWalton & Hersham 6-3 Dorchester Town | Southern League - Premier South |
| 12 | Sat 26 Aug 2023 | 10-2 v Chesham UnitedDorchester Town 0-2 Chesham United | Southern League - Premier South |
| 13 | Mon 28 Aug 2023 | 12-1 v Poole TownPoole Town 1-2 Dorchester Town | Southern League - Premier South |
| 14 | Sat 2 Sep 2023 | 10-2 v Plymouth ParkwayPlymouth Parkway 2-0 Dorchester Town | Emirates FA Cup First Qualifying Round |
| 15 | Sat 9 Sep 2023 | 12-1 v Swindon SupermarineDorchester Town 2-1 Swindon Supermarine | Southern League - Premier South |
| 16 | Tue 12 Sep 2023 | 11-1 v Hungerford TownHungerford Town 1-1 Dorchester Town | Southern League - Premier South |
| 17 | Sat 23 Sep 2023 | 13-1 v Didcot TownDorchester Town 3-1 Didcot Town | Southern League - Premier South |
| 18 | Tue 26 Sep 2023 | 10-5 v Plymouth ParkwayPlymouth Parkway 5-0 Dorchester Town | Southern League - Premier South |
| 19 | Sat 7 Oct 2023 | 11-3 v Merthyr TownMerthyr Town 3-1 Dorchester Town | Isuzu FA Trophy Third Qualifying Round |
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