| 1 | Sat 14 Aug 2021 | 71-2 v Beaconsfield TownDorchester Town 1-2 Beaconsfield Town | Southern League - Premier South |
| 2 | Tue 17 Aug 2021 | 71-2 v Taunton TownTaunton Town 2-1 Dorchester Town | Southern League - Premier South |
| 3 | Sat 21 Aug 2021 | 73-1 v HendonHendon 1-3 Dorchester Town | Southern League - Premier South |
| 4 | Sat 28 Aug 2021 | 7 0-1 v SalisburyDorchester Town 0-1 Salisbury | Southern League - Premier South |
| 5 | Mon 30 Aug 2021 | 70-1 v Poole TownPoole Town 1-0 Dorchester Town | Southern League - Premier South |
| 6 | Sat 4 Sep 2021 | 71-3 v Yate TownDorchester Town 1-3 Yate Town | Emirates FA Cup First Qualifying Round |
| 7 | Sat 11 Sep 2021 | 142-0 v Walton CasualsDorchester Town 2-0 Walton Casuals | Southern League - Premier South |
| 8 | Tue 14 Sep 2021 | 2 0-1 v Weston-super-MareDorchester Town 0-1 Weston-super-Mare | Southern League - Premier South |
| 9 | Sat 25 Sep 2021 | 120-2 v Harrow BoroughHarrow Borough 2-0 Dorchester Town | Southern League - Premier South |
| 10 | Sat 2 Oct 2021 | 150-2 v Gosport BoroughDorchester Town 0-2 Gosport Borough | Southern League - Premier South |
| 11 | Sat 9 Oct 2021 | 20-1 v Hayes & Yeading UnitedDorchester Town 0-1 Hayes & Yeading United | Southern League - Premier South |
| 12 | Wed 13 Oct 2021 | 23-2 v Tiverton TownTiverton Town 2-3 Dorchester Town | Southern League - Premier South |
| 13 | Sat 16 Oct 2021 | 21-5 v Chesham UnitedChesham United 5-1 Dorchester Town | Southern League - Premier South |
| 14 | Tue 19 Oct 2021 | 23-2 v Hartley WintneyDorchester Town 3-2 Hartley Wintney | Southern League - Premier South |
| 15 | Sat 23 Oct 2021 | 2 1-2 v FarnboroughDorchester Town 1-2 Farnborough | Southern League - Premier South |
| 16 | Sat 30 Oct 2021 | 20-2 v AFC TottonAFC Totton 2-0 Dorchester Town | Buildbase FA Trophy Third Qualifying Round |
| 17 | Tue 9 Nov 2021 | 21-1 v Merthyr TownMerthyr Town 1-1 Dorchester Town | Southern League - Premier South |
| 18 | Sat 13 Nov 2021 | 22-0 v Kings LangleyDorchester Town 2-0 Kings Langley | Southern League - Premier South |
| 19 | Tue 16 Nov 2021 | 23-0 v Wimborne TownDorchester Town 3-0 Wimborne Town | Southern League - Premier South |
| 20 | Tue 23 Nov 2021 | 20-1 v Truro CityTruro City 1-0 Dorchester Town | Southern League - Premier South |
| 21 | Sat 27 Nov 2021 | 20-1 v Weston-super-MareWeston-super-Mare 1-0 Dorchester Town | Southern League - Premier South |
| 22 | Sat 4 Dec 2021 | 23-1 v Harrow BoroughDorchester Town 3-1 Harrow Borough | Southern League - Premier South |
| 23 | Sat 11 Dec 2021 | 21-1 v Gosport BoroughGosport Borough 1-1 Dorchester Town | Southern League - Premier South |
| 24 | Mon 27 Dec 2021 | 81-4 v Poole TownDorchester Town 1-4 Poole Town | Southern League - Premier South |
| 25 | Sat 1 Jan 2022 | 71-2 v Yate TownYate Town 2-1 Dorchester Town | Southern League - Premier South |
| 26 | Sat 8 Jan 2022 | 20-1 v Taunton TownDorchester Town 0-1 Taunton Town | Southern League - Premier South |
| 27 | Sat 15 Jan 2022 | 20-2 v Beaconsfield TownBeaconsfield Town 2-0 Dorchester Town | Southern League - Premier South |
| 28 | Sat 22 Jan 2022 | 21-2 v Chesham UnitedDorchester Town 1-2 Chesham United | Southern League - Premier South |
| 29 | Tue 25 Jan 2022 | 2 1-1 v Truro CityDorchester Town 1-1 Truro City | Southern League - Premier South |
| 30 | Sat 29 Jan 2022 | 20-3 v Hayes & Yeading UnitedHayes & Yeading United 3-0 Dorchester Town | Southern League - Premier South |
| 31 | Sat 5 Feb 2022 | 2 1-1 v Tiverton TownDorchester Town 1-1 Tiverton Town | Southern League - Premier South |
| 32 | Sat 12 Feb 2022 | 20-1 v Hartley WintneyHartley Wintney 1-0 Dorchester Town | Southern League - Premier South |
| 33 | Sat 26 Feb 2022 | 22-1 v Swindon SupermarineDorchester Town 2-1 Swindon Supermarine | Southern League - Premier South |
| 34 | Sat 5 Mar 2022 | 21-3 v Merthyr TownDorchester Town 1-3 Merthyr Town | Southern League - Premier South |
| 35 | Sat 19 Mar 2022 | 22-1 v Kings LangleyKings Langley 1-2 Dorchester Town | Southern League - Premier South |
| 36 | Tue 22 Mar 2022 | 20-1 v FarnboroughFarnborough 1-0 Dorchester Town | Southern League - Premier South |
| 37 | Sat 26 Mar 2022 | 20-1 v Metropolitan PoliceDorchester Town 0-1 Metropolitan Police | Southern League - Premier South |
| 38 | Sat 2 Apr 2022 | 21-0 v Wimborne TownWimborne Town 0-1 Dorchester Town | Southern League - Premier South |
| 39 | Sat 9 Apr 2022 | 23-0 v HendonDorchester Town 3-0 Hendon | Southern League - Premier South |
| 40 | Sat 16 Apr 2022 | 21-0 v SalisburySalisbury 0-1 Dorchester Town | Southern League - Premier South |
| 41 | Mon 18 Apr 2022 | 20-1 v Yate TownDorchester Town 0-1 Yate Town | Southern League - Premier South |
| 42 | Sat 23 Apr 2022 | 21-1 v Walton CasualsWalton Casuals 1-1 Dorchester Town | Southern League - Premier South |
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