| 1 | Fri 11 Jul | 33-0 v Hamworthy UnitedHamworthy United 0-3 Dorchester Town | Friendly |
| 2 | Tue 15 Jul | 30-0 v Hamworthy RecreationHamworthy Recreation 0-0 Dorchester Town | Friendly |
| 3 | Sat 19 Jul | 36-1 v BridportDorchester Town 6-1 Bridport | Friendly |
| 4 | Tue 29 Jul | 32-2 v Cobham SportsCobham Sports 2-2 Dorchester Town | Friendly |
| 5 | Sat 2 Aug | 32-0 v Exmouth TownDorchester Town 2-0 Exmouth Town | Friendly |
| 6 | Sat 9 Aug | 30-0 v UxbridgeUxbridge 0-0 Dorchester Town | Southern League - Premier South |
| 7 | Tue 12 Aug | 31-3 v Tiverton TownDorchester Town 1-3 Tiverton Town | Southern League - Premier South |
| 8 | Sat 23 Aug | 30-1 v BerkhamstedBerkhamsted 1-0 Dorchester Town | Southern League - Premier South |
| 9 | Mon 25 Aug | 31-3 v Farnham TownDorchester Town 1-3 Farnham Town | Southern League - Premier South |
| 10 | Sat 30 Aug | 31-0 v SlimbridgeSlimbridge 0-1 Dorchester Town | Emirates FA Cup First Qualifying Round |
| 11 | Sat 6 Sep | 30-2 v Gloucester CityGloucester City 2-0 Dorchester Town | Southern League - Premier South |
| 12 | Tue 9 Sep | 33-3 v Plymouth ParkwayPlymouth Parkway 3-3 Dorchester Town | Southern League - Premier South |
| 13 | Sat 13 Sep | 33-1 v Brixham AFCBrixham AFC 1-3 Dorchester Town | Emirates FA Cup Second Qualifying Round |
| 14 | Sat 20 Sep | 32-0 v Yate TownDorchester Town 2-0 Yate Town | Southern League - Premier South |
| 15 | Tue 23 Sep | 31-4 v Taunton TownDorchester Town 1-4 Taunton Town | Southern League - Premier South |
| 16 | Sat 27 Sep | 30-3 v Farnham TownFarnham Town 3-0 Dorchester Town | Emirates FA Cup Third Qualifying Round |
| 17 | Sat 4 Oct | 34-0 v BidefordDorchester Town 4-0 Bideford | Isuzu FA Trophy Third Qualifying Round |
| 18 | Sat 11 Oct | 32-0 v Hanwell TownHanwell Town 0-2 Dorchester Town | Southern League - Premier South |
| 19 | Tue 14 Oct | 30-2 v Poole TownPoole Town 2-0 Dorchester Town | Southern League - Premier South |
| 20 | Sat 18 Oct | 30-2 v Wimborne TownDorchester Town 0-2 Wimborne Town | Southern League - Premier South |
| 21 | Tue 28 Oct | 31-1 v Basingstoke TownBasingstoke Town 1-1 Dorchester Town | Isuzu FA Trophy First Round |
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