| 1 | Fri 11 Jul | 153-0 v Hamworthy UnitedHamworthy United 0-3 Dorchester Town | Friendly |
| 2 | Tue 15 Jul | 150-0 v Hamworthy RecreationHamworthy Recreation 0-0 Dorchester Town | Friendly |
| 3 | Sat 19 Jul | 156-1 v BridportDorchester Town 6-1 Bridport | Friendly |
| 4 | Tue 29 Jul | 152-2 v Cobham SportsCobham Sports 2-2 Dorchester Town | Friendly |
| 5 | Sat 2 Aug | 152-0 v Exmouth TownDorchester Town 2-0 Exmouth Town | Friendly |
| 6 | Sat 9 Aug | 150-0 v UxbridgeUxbridge 0-0 Dorchester Town | Southern League - Premier South |
| 7 | Tue 12 Aug | 15 1-3 v Tiverton TownDorchester Town 1-3 Tiverton Town | Southern League - Premier South |
| 8 | Sat 16 Aug | 153-3 v Walton & HershamDorchester Town 3-3 Walton & Hersham | Southern League - Premier South |
| 9 | Sat 23 Aug | 150-1 v BerkhamstedBerkhamsted 1-0 Dorchester Town | Southern League - Premier South |
| 10 | Mon 25 Aug | 151-3 v Farnham TownDorchester Town 1-3 Farnham Town | Southern League - Premier South |
| 11 | Sat 6 Sep | 150-2 v Gloucester CityGloucester City 2-0 Dorchester Town | Southern League - Premier South |
| 12 | Sat 20 Sep | 152-0 v Yate TownDorchester Town 2-0 Yate Town | Southern League - Premier South |
| 13 | Tue 23 Sep | 151-4 v Taunton TownDorchester Town 1-4 Taunton Town | Southern League - Premier South |
| 14 | Sat 27 Sep | 150-3 v Farnham TownFarnham Town 3-0 Dorchester Town | Emirates FA Cup Third Qualifying Round |
| 15 | Sat 4 Oct | 154-0 v BidefordDorchester Town 4-0 Bideford | Isuzu FA Trophy Third Qualifying Round |
| 16 | Sat 11 Oct | 152-0 v Hanwell TownHanwell Town 0-2 Dorchester Town | Southern League - Premier South |
| 17 | Tue 14 Oct | 150-2 v Poole TownPoole Town 2-0 Dorchester Town | Southern League - Premier South |
| 18 | Sat 18 Oct | 150-2 v Wimborne TownDorchester Town 0-2 Wimborne Town | Southern League - Premier South |
| 19 | Tue 21 Oct | 15 1-0 v Basingstoke TownDorchester Town 1-0 Basingstoke Town | Southern League - Premier South |
| 20 | Tue 28 Oct | 151-1 v Basingstoke TownBasingstoke Town 1-1 Dorchester Town | Isuzu FA Trophy First Round |
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