| 1 | Fri 12 Jul | 154-0 v Hamworthy UnitedHamworthy United 0-4 Dorchester Town | Friendly |
| 2 | Sat 20 Jul | 63-1 v Rayners LaneDorchester Town 3-1 Rayners Lane | Friendly |
| 3 | Tue 23 Jul | 66-1 v BashleyBashley 1-6 Dorchester Town | Friendly |
| 4 | Tue 30 Jul | 61-2 v Larkhall AthleticDorchester Town 1-2 Larkhall Athletic | Friendly |
| 5 | Sat 3 Aug | 62-0 v WeymouthWeymouth 0-2 Dorchester Town | Friendly |
| 6 | Sat 10 Aug | 61-1 v Havant & WaterloovilleDorchester Town 1-1 Havant & Waterlooville | Southern League - Premier South |
| 7 | Tue 13 Aug | 61-1 v Tiverton TownTiverton Town 1-1 Dorchester Town | Southern League - Premier South |
| 8 | Sat 17 Aug | 60-2 v Basingstoke TownBasingstoke Town 2-0 Dorchester Town | Southern League - Premier South |
| 9 | Sat 24 Aug | 61-0 v Gloucester CityDorchester Town 1-0 Gloucester City | Southern League - Premier South |
| 10 | Sat 31 Aug | 60-2 v Banbury UnitedBanbury United 2-0 Dorchester Town | Emirates FA Cup First Qualifying Round |
| 11 | Sat 7 Sep | 64-0 v Frome TownDorchester Town 4-0 Frome Town | Southern League - Premier South |
| 12 | Sat 14 Sep | 63-2 v AFC TottonDorchester Town 3-2 AFC Totton | Southern League - Premier South |
| 13 | Sat 21 Sep | 63-1 v Chertsey TownDorchester Town 3-1 Chertsey Town | Southern League - Premier South |
| 14 | Sat 5 Oct | 60-0 v Tiverton TownTiverton Town 0-0 Dorchester Town | Isuzu FA Trophy Third Qualifying Round |
| 15 | Sat 12 Oct | 62-2 v MarlowMarlow 2-2 Dorchester Town | Southern League - Premier South |
| 16 | Tue 15 Oct | 65-1 v SholingSholing 1-5 Dorchester Town | Southern League - Premier South |
| 17 | Sat 19 Oct | 60-3 v Hanwell TownDorchester Town 0-3 Hanwell Town | Southern League - Premier South |
| 18 | Tue 22 Oct | 61-0 v Plymouth ParkwayDorchester Town 1-0 Plymouth Parkway | Southern League - Premier South |
| 19 | Sat 26 Oct | 60-1 v AFC TottonAFC Totton 1-0 Dorchester Town | Isuzu FA Trophy First Round |
| 20 | Sat 2 Nov | 60-1 v Swindon SupermarineSwindon Supermarine 1-0 Dorchester Town | Southern League - Premier South |
| 21 | Sat 9 Nov | 61-1 v Bracknell TownBracknell Town 1-1 Dorchester Town | Southern League - Premier South |
| 22 | Wed 13 Nov | 62-2 v Gosport BoroughGosport Borough 2-2 Dorchester Town | Southern League - Premier South |
| 23 | Sat 16 Nov | 62-2 v Merthyr TownDorchester Town 2-2 Merthyr Town | Southern League - Premier South |
| 24 | Sat 23 Nov | 6 1-1 v Taunton TownDorchester Town 1-1 Taunton Town | Southern League - Premier South |
| 25 | Sat 30 Nov | 6 1-1 v Wimborne TownWimborne Town 1-1 Dorchester Town | Southern League - Premier South |
| 26 | Sat 14 Dec | 62-2 v Walton & HershamWalton & Hersham 2-2 Dorchester Town | Southern League - Premier South |
| 27 | Sat 21 Dec | 65-0 v Tiverton TownDorchester Town 5-0 Tiverton Town | Southern League - Premier South |
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