| 1 | Sat 20 Jul | 23-1 v Rayners LaneDorchester Town 3-1 Rayners Lane | Friendly |
| 2 | Tue 23 Jul | 26-1 v BashleyBashley 1-6 Dorchester Town | Friendly |
| 3 | Sat 27 Jul | 152-1 v Bemerton Heath HarlequinsDorchester Town 2-1 Bemerton Heath Harlequins | Friendly |
| 4 | Tue 30 Jul | 21-2 v Larkhall AthleticDorchester Town 1-2 Larkhall Athletic | Friendly |
| 5 | Sat 3 Aug | 22-0 v WeymouthWeymouth 0-2 Dorchester Town | Friendly |
| 6 | Sat 10 Aug | 21-1 v Havant & WaterloovilleDorchester Town 1-1 Havant & Waterlooville | Southern League - Premier South |
| 7 | Tue 13 Aug | 21-1 v Tiverton TownTiverton Town 1-1 Dorchester Town | Southern League - Premier South |
| 8 | Sat 17 Aug | 20-2 v Basingstoke TownBasingstoke Town 2-0 Dorchester Town | Southern League - Premier South |
| 9 | Sat 24 Aug | 21-0 v Gloucester CityDorchester Town 1-0 Gloucester City | Southern League - Premier South |
| 10 | Wed 28 Aug | 20-0 v Winchester CityWinchester City 0-0 Dorchester Town | Southern League - Premier South |
| 11 | Sat 31 Aug | 20-2 v Banbury UnitedBanbury United 2-0 Dorchester Town | Emirates FA Cup First Qualifying Round |
| 12 | Sat 7 Sep | 24-0 v Frome TownDorchester Town 4-0 Frome Town | Southern League - Premier South |
| 13 | Sat 14 Sep | 23-2 v AFC TottonDorchester Town 3-2 AFC Totton | Southern League - Premier South |
| 14 | Sat 21 Sep | 23-1 v Chertsey TownDorchester Town 3-1 Chertsey Town | Southern League - Premier South |
| 15 | Sat 5 Oct | 20-0 v Tiverton TownTiverton Town 0-0 Dorchester Town | Isuzu FA Trophy Third Qualifying Round |
| 16 | Sat 12 Oct | 22-2 v MarlowMarlow 2-2 Dorchester Town | Southern League - Premier South |
| 17 | Tue 15 Oct | 25-1 v SholingSholing 1-5 Dorchester Town | Southern League - Premier South |
| 18 | Sat 19 Oct | 20-3 v Hanwell TownDorchester Town 0-3 Hanwell Town | Southern League - Premier South |
| 19 | Tue 22 Oct | 21-0 v Plymouth ParkwayDorchester Town 1-0 Plymouth Parkway | Southern League - Premier South |
| 20 | Sat 26 Oct | 20-1 v AFC TottonAFC Totton 1-0 Dorchester Town | Isuzu FA Trophy First Round |
| 21 | Sat 2 Nov | 20-1 v Swindon SupermarineSwindon Supermarine 1-0 Dorchester Town | Southern League - Premier South |
| 22 | Sat 9 Nov | 21-1 v Bracknell TownBracknell Town 1-1 Dorchester Town | Southern League - Premier South |
| 23 | Wed 13 Nov | 22-2 v Gosport BoroughGosport Borough 2-2 Dorchester Town | Southern League - Premier South |
| 24 | Sat 16 Nov | 22-2 v Merthyr TownDorchester Town 2-2 Merthyr Town | Southern League - Premier South |
| 25 | Sat 23 Nov | 21-1 v Taunton TownDorchester Town 1-1 Taunton Town | Southern League - Premier South |
| 26 | Sat 30 Nov | 21-1 v Wimborne TownWimborne Town 1-1 Dorchester Town | Southern League - Premier South |
| 27 | Sat 7 Dec | 24-2 v Hungerford TownDorchester Town 4-2 Hungerford Town | Southern League - Premier South |
| 28 | Sat 14 Dec | 22-2 v Walton & HershamWalton & Hersham 2-2 Dorchester Town | Southern League - Premier South |
| 29 | Sat 21 Dec | 25-0 v Tiverton TownDorchester Town 5-0 Tiverton Town | Southern League - Premier South |
| 30 | Thu 26 Dec | 21-1 v Poole TownPoole Town 1-1 Dorchester Town | Southern League - Premier South |
| 31 | Sat 28 Dec | 23-2 v Basingstoke TownDorchester Town 3-2 Basingstoke Town | Southern League - Premier South |
| 32 | Wed 1 Jan | 21-0 v Winchester CityDorchester Town 1-0 Winchester City | Southern League - Premier South |
| 33 | Sat 4 Jan | 21-1 v Havant & WaterloovilleHavant & Waterlooville 1-1 Dorchester Town | Southern League - Premier South |
| 34 | Sat 11 Jan | 20-0 v Merthyr TownMerthyr Town 0-0 Dorchester Town | Southern League - Premier South |
| 35 | Sat 18 Jan | 21-0 v Bracknell TownDorchester Town 1-0 Bracknell Town | Southern League - Premier South |
| 36 | Sat 25 Jan | 21-1 v SholingDorchester Town 1-1 Sholing | Southern League - Premier South |
| 37 | Sat 8 Feb | 24-1 v Swindon SupermarineDorchester Town 4-1 Swindon Supermarine | Southern League - Premier South |
| 38 | Sat 15 Feb | 22-1 v Plymouth ParkwayPlymouth Parkway 1-2 Dorchester Town | Southern League - Premier South |
| 39 | Sat 22 Feb | 21-1 v Wimborne TownDorchester Town 1-1 Wimborne Town | Southern League - Premier South |
| 40 | Sat 1 Mar | 21-1 v Taunton TownTaunton Town 1-1 Dorchester Town | Southern League - Premier South |
| 41 | Tue 4 Mar | 2 0-3 v Hanwell TownHanwell Town 3-0 Dorchester Town | Southern League - Premier South |
| 42 | Sat 8 Mar | 20-2 v Gosport BoroughDorchester Town 0-2 Gosport Borough | Southern League - Premier South |
| 43 | Sat 15 Mar | 21-0 v Chertsey TownChertsey Town 0-1 Dorchester Town | Southern League - Premier South |
| 44 | Sat 22 Mar | 26-0 v MarlowDorchester Town 6-0 Marlow | Southern League - Premier South |
| 45 | Sat 29 Mar | 21-1 v AFC TottonAFC Totton 1-1 Dorchester Town | Southern League - Premier South |
| 46 | Sat 5 Apr | 23-3 v Gloucester CityGloucester City 3-3 Dorchester Town | Southern League - Premier South |
| 47 | Sat 12 Apr | 21-0 v Walton & HershamDorchester Town 1-0 Walton & Hersham | Southern League - Premier South |
| 48 | Fri 18 Apr | 23-2 v Frome TownFrome Town 2-3 Dorchester Town | Southern League - Premier South |
| 49 | Mon 21 Apr | 23-2 v Poole TownDorchester Town 3-2 Poole Town | Southern League - Premier South |
| 50 | Sat 26 Apr | 22-1 v Hungerford TownHungerford Town 1-2 Dorchester Town | Southern League - Premier South |
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