| 1 | Tue 11 Aug | 81-2 v Westbury UnitedPortland United 1-2 Westbury United | Southern League - South Division |
| 2 | Sat 15 Aug | 80-0 v Bristol Manor FarmBristol Manor Farm 0-0 Portland United | Southern League - South Division |
| 3 | Mon 31 Aug | 82-0 v ShaftesburyPortland United 2-0 Shaftesbury | Southern League - South Division |
| 4 | Wed 16 Sep | 43-3 v Paulton RoversPaulton Rovers 3-3 Portland United | Southern League - South Division |
| 5 | Sat 19 Sep | 4 4-1 v Larkhall AthleticPortland United 4-1 Larkhall Athletic | Southern League - South Division |
| 6 | Tue 29 Sep | 81-2 v Falmouth TownPortland United 1-2 Falmouth Town | Southern League - South Division |
| 7 | Sat 3 Oct | 15 2-1 v BidefordBideford 1-2 Portland United | Southern League - South Division |
| 8 | Wed 7 Oct | 80-1 v SlimbridgeSlimbridge 1-0 Portland United | Southern League - South Division |
| 9 | Sat 17 Oct | 8 4-1 v Tiverton TownTiverton Town 1-4 Portland United | Southern League - South Division |
| 10 | Tue 20 Oct | 8 0-6 v Melksham TownMelksham Town 6-0 Portland United | Southern League - South Division |
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