| 1 | Tue 15 Jul | 40-0 v Hamworthy RecreationHamworthy Recreation 0-0 Dorchester Town | Friendly |
| 2 | Sat 16 Aug | 43-3 v Walton & HershamDorchester Town 3-3 Walton & Hersham | Southern League - Premier South |
| 3 | Sat 23 Aug | 4 0-1 v BerkhamstedBerkhamsted 1-0 Dorchester Town | Southern League - Premier South |
| 4 | Mon 25 Aug | 41-3 v Farnham TownDorchester Town 1-3 Farnham Town | Southern League - Premier South |
| 5 | Sat 30 Aug | 41-0 v SlimbridgeSlimbridge 0-1 Dorchester Town | Emirates FA Cup First Qualifying Round |
| 6 | Sat 6 Sep | 4 0-2 v Gloucester CityGloucester City 2-0 Dorchester Town | Southern League - Premier South |
| 7 | Tue 9 Sep | 43-3 v Plymouth ParkwayPlymouth Parkway 3-3 Dorchester Town | Southern League - Premier South |
| 8 | Sat 13 Sep | 43-1 v Brixham AFCBrixham AFC 1-3 Dorchester Town | Emirates FA Cup Second Qualifying Round |
| 9 | Sat 20 Sep | 42-0 v Yate TownDorchester Town 2-0 Yate Town | Southern League - Premier South |
| 10 | Tue 23 Sep | 41-4 v Taunton TownDorchester Town 1-4 Taunton Town | Southern League - Premier South |
| 11 | Sat 27 Sep | 40-3 v Farnham TownFarnham Town 3-0 Dorchester Town | Emirates FA Cup Third Qualifying Round |
| 12 | Sat 4 Oct | 44-0 v BidefordDorchester Town 4-0 Bideford | Isuzu FA Trophy Third Qualifying Round |
| 13 | Sat 11 Oct | 42-0 v Hanwell TownHanwell Town 0-2 Dorchester Town | Southern League - Premier South |
| 14 | Tue 14 Oct | 4 0-2 v Poole TownPoole Town 2-0 Dorchester Town | Southern League - Premier South |
| 15 | Sat 18 Oct | 40-2 v Wimborne TownDorchester Town 0-2 Wimborne Town | Southern League - Premier South |
| 16 | Tue 21 Oct | 41-0 v Basingstoke TownDorchester Town 1-0 Basingstoke Town | Southern League - Premier South |
| 17 | Tue 28 Oct | 41-1 v Basingstoke TownBasingstoke Town 1-1 Dorchester Town | Isuzu FA Trophy First Round |
| 18 | Sat 8 Nov | 40-0 v Chertsey TownDorchester Town 0-0 Chertsey Town | Southern League - Premier South |
| 19 | Sat 15 Nov | 4 0-2 v Dover AthleticDover Athletic 2-0 Dorchester Town | Isuzu FA Trophy Second Round |
| 20 | Tue 18 Nov | 42-2 v Plymouth ParkwayDorchester Town 2-2 Plymouth Parkway | Southern League - Premier South |
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