| 1 | Sat 10 Aug | 11-1 v Havant & WaterloovilleDorchester Town 1-1 Havant & Waterlooville | Southern League - Premier South |
| 2 | Sat 24 Aug | 11-0 v Gloucester CityDorchester Town 1-0 Gloucester City | Southern League - Premier South |
| 3 | Wed 28 Aug | 10-0 v Winchester CityWinchester City 0-0 Dorchester Town | Southern League - Premier South |
| 4 | Sat 31 Aug | 10-2 v Banbury UnitedBanbury United 2-0 Dorchester Town | Emirates FA Cup First Qualifying Round |
| 5 | Sat 14 Sep | 13-2 v AFC TottonDorchester Town 3-2 AFC Totton | Southern League - Premier South |
| 6 | Sat 21 Sep | 13-1 v Chertsey TownDorchester Town 3-1 Chertsey Town | Southern League - Premier South |
| 7 | Sat 5 Oct | 10-0 v Tiverton TownTiverton Town 0-0 Dorchester Town | Isuzu FA Trophy Third Qualifying Round |
| 8 | Sat 12 Oct | 12-2 v MarlowMarlow 2-2 Dorchester Town | Southern League - Premier South |
| 9 | Tue 15 Oct | 15-1 v SholingSholing 1-5 Dorchester Town | Southern League - Premier South |
| 10 | Sat 19 Oct | 10-3 v Hanwell TownDorchester Town 0-3 Hanwell Town | Southern League - Premier South |
| 11 | Tue 22 Oct | 11-0 v Plymouth ParkwayDorchester Town 1-0 Plymouth Parkway | Southern League - Premier South |
| 12 | Sat 26 Oct | 10-1 v AFC TottonAFC Totton 1-0 Dorchester Town | Isuzu FA Trophy First Round |
| 13 | Sat 2 Nov | 10-1 v Swindon SupermarineSwindon Supermarine 1-0 Dorchester Town | Southern League - Premier South |
| 14 | Sat 9 Nov | 11-1 v Bracknell TownBracknell Town 1-1 Dorchester Town | Southern League - Premier South |
| 15 | Wed 13 Nov | 12-2 v Gosport BoroughGosport Borough 2-2 Dorchester Town | Southern League - Premier South |
| 16 | Sat 16 Nov | 12-2 v Merthyr TownDorchester Town 2-2 Merthyr Town | Southern League - Premier South |
| 17 | Sat 23 Nov | 11-1 v Taunton TownDorchester Town 1-1 Taunton Town | Southern League - Premier South |
| 18 | Sat 30 Nov | 11-1 v Wimborne TownWimborne Town 1-1 Dorchester Town | Southern League - Premier South |
| 19 | Sat 7 Dec | 14-2 v Hungerford TownDorchester Town 4-2 Hungerford Town | Southern League - Premier South |
| 20 | Sat 14 Dec | 12-2 v Walton & HershamWalton & Hersham 2-2 Dorchester Town | Southern League - Premier South |
| 21 | Sat 21 Dec | 15-0 v Tiverton TownDorchester Town 5-0 Tiverton Town | Southern League - Premier South |
| 22 | Thu 26 Dec | 11-1 v Poole TownPoole Town 1-1 Dorchester Town | Southern League - Premier South |
| 23 | Sat 28 Dec | 13-2 v Basingstoke TownDorchester Town 3-2 Basingstoke Town | Southern League - Premier South |
| 24 | Wed 1 Jan | 11-0 v Winchester CityDorchester Town 1-0 Winchester City | Southern League - Premier South |
| 25 | Sat 4 Jan | 11-1 v Havant & WaterloovilleHavant & Waterlooville 1-1 Dorchester Town | Southern League - Premier South |
| 26 | Sat 11 Jan | 10-0 v Merthyr TownMerthyr Town 0-0 Dorchester Town | Southern League - Premier South |
| 27 | Sat 18 Jan | 11-0 v Bracknell TownDorchester Town 1-0 Bracknell Town | Southern League - Premier South |
| 28 | Sat 1 Mar | 11-1 v Taunton TownTaunton Town 1-1 Dorchester Town | Southern League - Premier South |
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