| 1 | Tue 4 Jul | 83-1 v BashleyDorchester Town 3-1 Bashley | Friendly |
| 2 | Sat 8 Jul | 50-1 v Weston-super-MareDorchester Town 0-1 Weston-super-Mare | Friendly |
| 3 | Tue 11 Jul | 152-0 v Portland UnitedPortland United 0-2 Dorchester Town | Friendly |
| 4 | Sat 15 Jul | 51-1 v Frome TownDorchester Town 1-1 Frome Town | Friendly |
| 5 | Tue 18 Jul | 50-5 v Yeovil TownDorchester Town 0-5 Yeovil Town | Friendly |
| 6 | Sat 22 Jul | 51-2 v Wimborne TownDorchester Town 1-2 Wimborne Town | Friendly |
| 7 | Tue 25 Jul | 53-0 v EastleighDorchester Town 3-0 Eastleigh | Friendly |
| 8 | Sat 5 Aug | 22-3 v Merthyr TownMerthyr Town 3-2 Dorchester Town | Southern League - Premier South |
| 9 | Sat 12 Aug | 52-2 v Harrow BoroughDorchester Town 2-2 Harrow Borough | Southern League - Premier South |
| 10 | Tue 15 Aug | 5 0-4 v Winchester CityDorchester Town 0-4 Winchester City | Southern League - Premier South |
| 11 | Sat 19 Aug | 53-6 v Walton & HershamWalton & Hersham 6-3 Dorchester Town | Southern League - Premier South |
| 12 | Sat 26 Aug | 50-2 v Chesham UnitedDorchester Town 0-2 Chesham United | Southern League - Premier South |
| 13 | Mon 28 Aug | 52-1 v Poole TownPoole Town 1-2 Dorchester Town | Southern League - Premier South |
| 14 | Sat 2 Sep | 50-2 v Plymouth ParkwayPlymouth Parkway 2-0 Dorchester Town | Emirates FA Cup First Qualifying Round |
| 15 | Sat 9 Sep | 52-1 v Swindon SupermarineDorchester Town 2-1 Swindon Supermarine | Southern League - Premier South |
| 16 | Tue 12 Sep | 51-1 v Hungerford TownHungerford Town 1-1 Dorchester Town | Southern League - Premier South |
| 17 | Sat 23 Sep | 53-1 v Didcot TownDorchester Town 3-1 Didcot Town | Southern League - Premier South |
| 18 | Tue 26 Sep | 50-5 v Plymouth ParkwayPlymouth Parkway 5-0 Dorchester Town | Southern League - Premier South |
| 19 | Sat 7 Oct | 51-3 v Merthyr TownMerthyr Town 3-1 Dorchester Town | Isuzu FA Trophy Third Qualifying Round |
| 20 | Wed 11 Oct | 52-2 v Gosport BoroughGosport Borough 2-2 Dorchester Town | Southern League - Premier South |
| 21 | Sat 21 Oct | 50-1 v HendonHendon 1-0 Dorchester Town | Southern League - Premier South |
| 22 | Tue 24 Oct | 51-2 v SholingDorchester Town 1-2 Sholing | Southern League - Premier South |
| 23 | Sat 28 Oct | 51-1 v Hayes & Yeading UnitedDorchester Town 1-1 Hayes & Yeading United | Southern League - Premier South |
| 24 | Sat 11 Nov | 54-1 v Basingstoke TownDorchester Town 4-1 Basingstoke Town | Southern League - Premier South |
| 25 | Tue 14 Nov | 51-2 v Bracknell TownDorchester Town 1-2 Bracknell Town | Southern League - Premier South |
| 26 | Sat 25 Nov | 52-3 v SalisburySalisbury 3-2 Dorchester Town | Southern League - Premier South |
| 27 | Sat 9 Dec | 52-1 v Swindon SupermarineSwindon Supermarine 1-2 Dorchester Town | Southern League - Premier South |
| 28 | Sat 16 Dec | 51-2 v Walton & HershamDorchester Town 1-2 Walton & Hersham | Southern League - Premier South |
| 29 | Tue 26 Dec | 51-2 v Poole TownDorchester Town 1-2 Poole Town | Southern League - Premier South |
| 30 | Sat 13 Jan | 52-0 v Harrow BoroughHarrow Borough 0-2 Dorchester Town | Southern League - Premier South |
| 31 | Sat 20 Jan | 53-2 v Merthyr TownDorchester Town 3-2 Merthyr Town | Southern League - Premier South |
| 32 | Sat 27 Jan | 50-0 v Plymouth ParkwayDorchester Town 0-0 Plymouth Parkway | Southern League - Premier South |
| 33 | Sat 3 Feb | 51-0 v Didcot TownDidcot Town 0-1 Dorchester Town | Southern League - Premier South |
| 34 | Tue 6 Feb | 51-1 v Hanwell TownHanwell Town 1-1 Dorchester Town | Southern League - Premier South |
| 35 | Sat 10 Feb | 50-3 v Gosport BoroughDorchester Town 0-3 Gosport Borough | Southern League - Premier South |
| 36 | Sat 17 Feb | 53-1 v Bracknell TownBracknell Town 1-3 Dorchester Town | Southern League - Premier South |
| 37 | Sat 24 Feb | 52-2 v HendonDorchester Town 2-2 Hendon | Southern League - Premier South |
| 38 | Wed 28 Feb | 54-4 v AFC TottonAFC Totton 4-4 Dorchester Town | Southern League - Premier South |
| 39 | Sat 9 Mar | 52-1 v Beaconsfield TownDorchester Town 2-1 Beaconsfield Town | Southern League - Premier South |
| 40 | Sat 16 Mar | 54-3 v Beaconsfield TownBeaconsfield Town 3-4 Dorchester Town | Southern League - Premier South |
| 41 | Sat 23 Mar | 51-0 v SalisburyDorchester Town 1-0 Salisbury | Southern League - Premier South |
| 42 | Sat 30 Mar | 51-1 v Winchester CityWinchester City 1-1 Dorchester Town | Southern League - Premier South |
| 43 | Mon 1 Apr | 52-1 v Tiverton TownDorchester Town 2-1 Tiverton Town | Southern League - Premier South |
| 44 | Sat 6 Apr | 51-0 v Hayes & Yeading UnitedHayes & Yeading United 0-1 Dorchester Town | Southern League - Premier South |
| 45 | Tue 9 Apr | 52-1 v SholingSholing 1-2 Dorchester Town | Southern League - Premier South |
| 46 | Sat 13 Apr | 52-1 v Hanwell TownDorchester Town 2-1 Hanwell Town | Southern League - Premier South |
| 47 | Tue 16 Apr | 52-0 v Tiverton TownTiverton Town 0-2 Dorchester Town | Southern League - Premier South |
| 48 | Sat 20 Apr | 51-3 v Basingstoke TownBasingstoke Town 3-1 Dorchester Town | Southern League - Premier South |
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