| 1 | Sat 2 Oct 2021 | 5 0-2 v Gosport BoroughDorchester Town 0-2 Gosport Borough | Southern League - Premier South |
| 2 | Sat 9 Oct 2021 | 40-1 v Hayes & Yeading UnitedDorchester Town 0-1 Hayes & Yeading United | Southern League - Premier South |
| 3 | Wed 13 Oct 2021 | 53-2 v Tiverton TownTiverton Town 2-3 Dorchester Town | Southern League - Premier South |
| 4 | Sat 16 Oct 2021 | 51-5 v Chesham UnitedChesham United 5-1 Dorchester Town | Southern League - Premier South |
| 5 | Tue 19 Oct 2021 | 43-2 v Hartley WintneyDorchester Town 3-2 Hartley Wintney | Southern League - Premier South |
| 6 | Sat 23 Oct 2021 | 41-2 v FarnboroughDorchester Town 1-2 Farnborough | Southern League - Premier South |
| 7 | Sat 30 Oct 2021 | 50-2 v AFC TottonAFC Totton 2-0 Dorchester Town | Buildbase FA Trophy Third Qualifying Round |
| 8 | Sat 6 Nov 2021 | 60-1 v Swindon SupermarineSwindon Supermarine 1-0 Dorchester Town | Southern League - Premier South |
| 9 | Tue 9 Nov 2021 | 6 1-1 v Merthyr TownMerthyr Town 1-1 Dorchester Town | Southern League - Premier South |
| 10 | Sat 13 Nov 2021 | 62-0 v Kings LangleyDorchester Town 2-0 Kings Langley | Southern League - Premier South |
| 11 | Tue 16 Nov 2021 | 63-0 v Wimborne TownDorchester Town 3-0 Wimborne Town | Southern League - Premier South |
| 12 | Sat 20 Nov 2021 | 40-2 v Metropolitan PoliceMetropolitan Police 2-0 Dorchester Town | Southern League - Premier South |
| 13 | Sat 27 Nov 2021 | 60-1 v Weston-super-MareWeston-super-Mare 1-0 Dorchester Town | Southern League - Premier South |
| 14 | Sat 4 Dec 2021 | 63-1 v Harrow BoroughDorchester Town 3-1 Harrow Borough | Southern League - Premier South |
| 15 | Sat 11 Dec 2021 | 121-1 v Gosport BoroughGosport Borough 1-1 Dorchester Town | Southern League - Premier South |
| 16 | Mon 27 Dec 2021 | 51-4 v Poole TownDorchester Town 1-4 Poole Town | Southern League - Premier South |
| 17 | Sat 29 Jan 2022 | 150-3 v Hayes & Yeading UnitedHayes & Yeading United 3-0 Dorchester Town | Southern League - Premier South |
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