| 1 | Fri 10 Jul | 25-1 v DowntonDorchester Town 5-1 Downton | Friendly |
| 2 | Sat 18 Jul | 23-1 v East Cowes Victoria AthleticDorchester Town 3-1 East Cowes Victoria Athletic | Friendly |
| 3 | Tue 21 Jul | 22-1 v BrockenhurstBrockenhurst 1-2 Dorchester Town | Friendly |
| 4 | Sat 25 Jul | 21-3 v BashleyBashley 3-1 Dorchester Town | Friendly |
| 5 | Sat 1 Aug | 21-2 v AFC PortchesterDorchester Town 1-2 AFC Portchester | Friendly |
| 6 | Sat 8 Aug | 2 1-5 v WeymouthWeymouth 5-1 Dorchester Town | Southern League - South Division |
| 7 | Sat 15 Aug | 23-2 v Willand RoversWilland Rovers 2-3 Dorchester Town | Southern League - South Division |
| 8 | Sat 22 Aug | 23-1 v Winchester CityDorchester Town 3-1 Winchester City | Emirates FA Cup Preliminary Round |
| 9 | Mon 31 Aug | 2 1-0 v Hungerford TownDorchester Town 1-0 Hungerford Town | Southern League - South Division |
| 10 | Sat 5 Sep | 23-2 v Brixham AFCBrixham AFC 2-3 Dorchester Town | Emirates FA Cup First Qualifying Round |
| 11 | Tue 15 Sep | 2 2-1 v Tiverton TownDorchester Town 2-1 Tiverton Town | Southern League - South Division |
| 12 | Sat 19 Sep | 20-2 v Oxford CityDorchester Town 0-2 Oxford City | Emirates FA Cup Second Qualifying Round |
| 13 | Sat 26 Sep | 2 4-1 v Exmouth TownDorchester Town 4-1 Exmouth Town | Southern League - South Division |
| 14 | Tue 29 Sep | 23-1 v BidefordBideford 1-3 Dorchester Town | Southern League - South Division |
| 15 | Sat 10 Oct | 22-1 v HartpuryDorchester Town 2-1 Hartpury | Southern League - South Division |
| 16 | Tue 13 Oct | 2 3-0 v Melksham TownDorchester Town 3-0 Melksham Town | Southern League - South Division |
| 17 | Sat 17 Oct | 23-1 v Sporting Club InkberrowSporting Club Inkberrow 1-3 Dorchester Town | Southern League - South Division |
| 18 | Sat 24 Oct | 20-2 v SlimbridgeDorchester Town 0-2 Slimbridge | Southern League - South Division |
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