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