| 1 | Fri 11 Jul | 23-0 v Hamworthy UnitedHamworthy United 0-3 Dorchester Town | Friendly |
| 2 | Tue 15 Jul | 20-0 v Hamworthy RecreationHamworthy Recreation 0-0 Dorchester Town | Friendly |
| 3 | Sat 16 Aug | 23-3 v Walton & HershamDorchester Town 3-3 Walton & Hersham | Southern League - Premier South |
| 4 | Sat 23 Aug | 20-1 v BerkhamstedBerkhamsted 1-0 Dorchester Town | Southern League - Premier South |
| 5 | Mon 25 Aug | 21-3 v Farnham TownDorchester Town 1-3 Farnham Town | Southern League - Premier South |
| 6 | Sat 30 Aug | 21-0 v SlimbridgeSlimbridge 0-1 Dorchester Town | Emirates FA Cup First Qualifying Round |
| 7 | Tue 28 Oct | 21-1 v Basingstoke TownBasingstoke Town 1-1 Dorchester Town | Isuzu FA Trophy First Round |
| 8 | Sat 1 Nov | 22-2 v Bracknell TownBracknell Town 2-2 Dorchester Town | Southern League - Premier South |
| 9 | Sat 8 Nov | 20-0 v Chertsey TownDorchester Town 0-0 Chertsey Town | Southern League - Premier South |
| 10 | Sat 15 Nov | 2 0-2 v Dover AthleticDover Athletic 2-0 Dorchester Town | Isuzu FA Trophy Second Round |
| 11 | Tue 18 Nov | 22-2 v Plymouth ParkwayDorchester Town 2-2 Plymouth Parkway | Southern League - Premier South |
| 12 | Sat 22 Nov | 2 1-4 v Evesham UnitedEvesham United 4-1 Dorchester Town | Southern League - Premier South |
| 13 | Wed 26 Nov | 2 1-1 v Taunton TownTaunton Town 1-1 Dorchester Town | Southern League - Premier South |
| 14 | Sat 29 Nov | 22-2 v Gosport BoroughDorchester Town 2-2 Gosport Borough | Southern League - Premier South |
| 15 | Sat 6 Dec | 22-1 v Hungerford TownDorchester Town 2-1 Hungerford Town | Southern League - Premier South |
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