| 1 | Fri 11 Jul | 73-0 v Hamworthy UnitedHamworthy United 0-3 Dorchester Town | Friendly |
| 2 | Tue 15 Jul | 70-0 v Hamworthy RecreationHamworthy Recreation 0-0 Dorchester Town | Friendly |
| 3 | Sat 19 Jul | 166-1 v BridportDorchester Town 6-1 Bridport | Friendly |
| 4 | Tue 29 Jul | 82-2 v Cobham SportsCobham Sports 2-2 Dorchester Town | Friendly |
| 5 | Sat 2 Aug | 162-0 v Exmouth TownDorchester Town 2-0 Exmouth Town | Friendly |
| 6 | Sat 9 Aug | 160-0 v UxbridgeUxbridge 0-0 Dorchester Town | Southern League - Premier South |
| 7 | Tue 12 Aug | 161-3 v Tiverton TownDorchester Town 1-3 Tiverton Town | Southern League - Premier South |
| 8 | Sat 16 Aug | 163-3 v Walton & HershamDorchester Town 3-3 Walton & Hersham | Southern League - Premier South |
| 9 | Sat 20 Sep | 162-0 v Yate TownDorchester Town 2-0 Yate Town | Southern League - Premier South |
| 10 | Tue 23 Sep | 161-4 v Taunton TownDorchester Town 1-4 Taunton Town | Southern League - Premier South |
| 11 | Sat 27 Sep | 160-3 v Farnham TownFarnham Town 3-0 Dorchester Town | Emirates FA Cup Third Qualifying Round |
| 12 | Sat 4 Oct | 164-0 v BidefordDorchester Town 4-0 Bideford | Isuzu FA Trophy Third Qualifying Round |
| 13 | Tue 14 Oct | 160-2 v Poole TownPoole Town 2-0 Dorchester Town | Southern League - Premier South |
| 14 | Sat 18 Oct | 160-2 v Wimborne TownDorchester Town 0-2 Wimborne Town | Southern League - Premier South |
| 15 | Tue 21 Oct | 161-0 v Basingstoke TownDorchester Town 1-0 Basingstoke Town | Southern League - Premier South |
| 16 | Tue 28 Oct | 161-1 v Basingstoke TownBasingstoke Town 1-1 Dorchester Town | Isuzu FA Trophy First Round |
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