| 1 | Sat 14 Aug 2021 | 1 1-2 v Beaconsfield TownDorchester Town 1-2 Beaconsfield Town | Southern League - Premier South |
| 2 | Tue 17 Aug 2021 | 11-2 v Taunton TownTaunton Town 2-1 Dorchester Town | Southern League - Premier South |
| 3 | Sat 21 Aug 2021 | 13-1 v HendonHendon 1-3 Dorchester Town | Southern League - Premier South |
| 4 | Sat 28 Aug 2021 | 10-1 v SalisburyDorchester Town 0-1 Salisbury | Southern League - Premier South |
| 5 | Mon 30 Aug 2021 | 10-1 v Poole TownPoole Town 1-0 Dorchester Town | Southern League - Premier South |
| 6 | Sat 11 Sep 2021 | 1 2-0 v Walton CasualsDorchester Town 2-0 Walton Casuals | Southern League - Premier South |
| 7 | Tue 14 Sep 2021 | 10-1 v Weston-super-MareDorchester Town 0-1 Weston-super-Mare | Southern League - Premier South |
| 8 | Sat 25 Sep 2021 | 10-2 v Harrow BoroughHarrow Borough 2-0 Dorchester Town | Southern League - Premier South |
| 9 | Tue 9 Nov 2021 | 11-1 v Merthyr TownMerthyr Town 1-1 Dorchester Town | Southern League - Premier South |
| 10 | Sat 13 Nov 2021 | 12-0 v Kings LangleyDorchester Town 2-0 Kings Langley | Southern League - Premier South |
| 11 | Tue 16 Nov 2021 | 13-0 v Wimborne TownDorchester Town 3-0 Wimborne Town | Southern League - Premier South |
| 12 | Sat 20 Nov 2021 | 10-2 v Metropolitan PoliceMetropolitan Police 2-0 Dorchester Town | Southern League - Premier South |
| 13 | Tue 23 Nov 2021 | 10-1 v Truro CityTruro City 1-0 Dorchester Town | Southern League - Premier South |
| 14 | Sat 27 Nov 2021 | 10-1 v Weston-super-MareWeston-super-Mare 1-0 Dorchester Town | Southern League - Premier South |
| 15 | Sat 4 Dec 2021 | 13-1 v Harrow BoroughDorchester Town 3-1 Harrow Borough | Southern League - Premier South |
| 16 | Sat 11 Dec 2021 | 11-1 v Gosport BoroughGosport Borough 1-1 Dorchester Town | Southern League - Premier South |
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