| 1 | Fri 12 Jul | 34-0 v Hamworthy UnitedHamworthy United 0-4 Dorchester Town | Friendly |
| 2 | Sat 20 Jul | 233-1 v Rayners LaneDorchester Town 3-1 Rayners Lane | Friendly |
| 3 | Sat 27 Jul | 32-1 v Bemerton Heath HarlequinsDorchester Town 2-1 Bemerton Heath Harlequins | Friendly |
| 4 | Tue 30 Jul | 161-2 v Larkhall AthleticDorchester Town 1-2 Larkhall Athletic | Friendly |
| 5 | Sat 3 Aug | 152-0 v WeymouthWeymouth 0-2 Dorchester Town | Friendly |
| 6 | Sat 10 Aug | 161-1 v Havant & WaterloovilleDorchester Town 1-1 Havant & Waterlooville | Southern League - Premier South |
| 7 | Sat 17 Aug | 140-2 v Basingstoke TownBasingstoke Town 2-0 Dorchester Town | Southern League - Premier South |
| 8 | Sat 24 Aug | 161-0 v Gloucester CityDorchester Town 1-0 Gloucester City | Southern League - Premier South |
| 9 | Sat 31 Aug | 170-2 v Banbury UnitedBanbury United 2-0 Dorchester Town | Emirates FA Cup First Qualifying Round |
| 10 | Sat 21 Sep | 173-1 v Chertsey TownDorchester Town 3-1 Chertsey Town | Southern League - Premier South |
| 11 | Sat 7 Dec | 64-2 v Hungerford TownDorchester Town 4-2 Hungerford Town | Southern League - Premier South |
| 12 | Sat 14 Dec | 32-2 v Walton & HershamWalton & Hersham 2-2 Dorchester Town | Southern League - Premier South |
| 13 | Sat 21 Dec | 205-0 v Tiverton TownDorchester Town 5-0 Tiverton Town | Southern League - Premier South |
| 14 | Thu 26 Dec | 201-1 v Poole TownPoole Town 1-1 Dorchester Town | Southern League - Premier South |
| 15 | Sat 28 Dec | 203-2 v Basingstoke TownDorchester Town 3-2 Basingstoke Town | Southern League - Premier South |
| 16 | Wed 1 Jan | 201-0 v Winchester CityDorchester Town 1-0 Winchester City | Southern League - Premier South |
| 17 | Sat 4 Jan | 201-1 v Havant & WaterloovilleHavant & Waterlooville 1-1 Dorchester Town | Southern League - Premier South |
| 18 | Sat 11 Jan | 200-0 v Merthyr TownMerthyr Town 0-0 Dorchester Town | Southern League - Premier South |
| 19 | Sat 18 Jan | 201-0 v Bracknell TownDorchester Town 1-0 Bracknell Town | Southern League - Premier South |
| 20 | Sat 25 Jan | 201-1 v SholingDorchester Town 1-1 Sholing | Southern League - Premier South |
| 21 | Sat 15 Feb | 202-1 v Plymouth ParkwayPlymouth Parkway 1-2 Dorchester Town | Southern League - Premier South |
| 22 | Sat 1 Mar | 201-1 v Taunton TownTaunton Town 1-1 Dorchester Town | Southern League - Premier South |
| 23 | Tue 4 Mar | 200-3 v Hanwell TownHanwell Town 3-0 Dorchester Town | Southern League - Premier South |
| 24 | Sat 8 Mar | 200-2 v Gosport BoroughDorchester Town 0-2 Gosport Borough | Southern League - Premier South |
| 25 | Sat 15 Mar | 201-0 v Chertsey TownChertsey Town 0-1 Dorchester Town | Southern League - Premier South |
| 26 | Sat 22 Mar | 206-0 v MarlowDorchester Town 6-0 Marlow | Southern League - Premier South |
| 27 | Sat 5 Apr | 203-3 v Gloucester CityGloucester City 3-3 Dorchester Town | Southern League - Premier South |
| 28 | Sat 26 Apr | 202-1 v Hungerford TownHungerford Town 1-2 Dorchester Town | Southern League - Premier South |
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