| 1 | Tue 11 Aug | 91-2 v Westbury UnitedPortland United 1-2 Westbury United | Southern League - South Division |
| 2 | Mon 31 Aug | 162-0 v ShaftesburyPortland United 2-0 Shaftesbury | Southern League - South Division |
| 3 | Wed 16 Sep | 9 3-3 v Paulton RoversPaulton Rovers 3-3 Portland United | Southern League - South Division |
| 4 | Sat 19 Sep | 174-1 v Larkhall AthleticPortland United 4-1 Larkhall Athletic | Southern League - South Division |
| 5 | Tue 29 Sep | 101-2 v Falmouth TownPortland United 1-2 Falmouth Town | Southern League - South Division |
| 6 | Tue 13 Oct | 163-2 v Exmouth TownPortland United 3-2 Exmouth Town | Southern League - South Division |
| 7 | Sat 17 Oct | 164-1 v Tiverton TownTiverton Town 1-4 Portland United | Southern League - South Division |
| 8 | Tue 20 Oct | 160-6 v Melksham TownMelksham Town 6-0 Portland United | Southern League - South Division |
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