| 1 | Sat 14 Aug 2021 | 6 1-2 v Beaconsfield TownDorchester Town 1-2 Beaconsfield Town | Southern League - Premier South |
| 2 | Tue 17 Aug 2021 | 4 1-2 v Taunton TownTaunton Town 2-1 Dorchester Town | Southern League - Premier South |
| 3 | Sat 21 Aug 2021 | 2 3-1 v HendonHendon 1-3 Dorchester Town | Southern League - Premier South |
| 4 | Sat 28 Aug 2021 | 20-1 v SalisburyDorchester Town 0-1 Salisbury | Southern League - Premier South |
| 5 | Mon 30 Aug 2021 | 20-1 v Poole TownPoole Town 1-0 Dorchester Town | Southern League - Premier South |
| 6 | Sat 4 Sep 2021 | 21-3 v Yate TownDorchester Town 1-3 Yate Town | Emirates FA Cup First Qualifying Round |
| 7 | Sat 11 Sep 2021 | 22-0 v Walton CasualsDorchester Town 2-0 Walton Casuals | Southern League - Premier South |
| 8 | Tue 14 Sep 2021 | 50-1 v Weston-super-MareDorchester Town 0-1 Weston-super-Mare | Southern League - Premier South |
| 9 | Sat 25 Sep 2021 | 50-2 v Harrow BoroughHarrow Borough 2-0 Dorchester Town | Southern League - Premier South |
| 10 | Tue 19 Oct 2021 | 153-2 v Hartley WintneyDorchester Town 3-2 Hartley Wintney | Southern League - Premier South |
| 11 | Sat 4 Dec 2021 | 123-1 v Harrow BoroughDorchester Town 3-1 Harrow Borough | Southern League - Premier South |
| 12 | Sat 11 Dec 2021 | 161-1 v Gosport BoroughGosport Borough 1-1 Dorchester Town | Southern League - Premier South |
| 13 | Mon 27 Dec 2021 | 21-4 v Poole TownDorchester Town 1-4 Poole Town | Southern League - Premier South |
| 14 | Sat 1 Jan 2022 | 21-2 v Yate TownYate Town 2-1 Dorchester Town | Southern League - Premier South |
| 15 | Sat 8 Jan 2022 | 50-1 v Taunton TownDorchester Town 0-1 Taunton Town | Southern League - Premier South |
| 16 | Sat 15 Jan 2022 | 50-2 v Beaconsfield TownBeaconsfield Town 2-0 Dorchester Town | Southern League - Premier South |
| 17 | Sat 22 Jan 2022 | 121-2 v Chesham UnitedDorchester Town 1-2 Chesham United | Southern League - Premier South |
| 18 | Tue 25 Jan 2022 | 41-1 v Truro CityDorchester Town 1-1 Truro City | Southern League - Premier South |
| 19 | Sat 29 Jan 2022 | 40-3 v Hayes & Yeading UnitedHayes & Yeading United 3-0 Dorchester Town | Southern League - Premier South |
| 20 | Sat 12 Feb 2022 | 140-1 v Hartley WintneyHartley Wintney 1-0 Dorchester Town | Southern League - Premier South |
| 21 | Sat 26 Feb 2022 | 62-1 v Swindon SupermarineDorchester Town 2-1 Swindon Supermarine | Southern League - Premier South |
| 22 | Sat 19 Mar 2022 | 62-1 v Kings LangleyKings Langley 1-2 Dorchester Town | Southern League - Premier South |
| 23 | Tue 22 Mar 2022 | 40-1 v FarnboroughFarnborough 1-0 Dorchester Town | Southern League - Premier South |
| 24 | Sat 26 Mar 2022 | 4 0-1 v Metropolitan PoliceDorchester Town 0-1 Metropolitan Police | Southern League - Premier South |
| 25 | Sat 2 Apr 2022 | 41-0 v Wimborne TownWimborne Town 0-1 Dorchester Town | Southern League - Premier South |
| 26 | Sat 9 Apr 2022 | 43-0 v HendonDorchester Town 3-0 Hendon | Southern League - Premier South |
| 27 | Sat 16 Apr 2022 | 41-0 v SalisburySalisbury 0-1 Dorchester Town | Southern League - Premier South |
| 28 | Mon 18 Apr 2022 | 80-1 v Yate TownDorchester Town 0-1 Yate Town | Southern League - Premier South |
| 29 | Sat 23 Apr 2022 | 41-1 v Walton CasualsWalton Casuals 1-1 Dorchester Town | Southern League - Premier South |
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