| 1 | Tue 11 Aug | 11-2 v Westbury UnitedPortland United 1-2 Westbury United | Southern League - South Division |
| 2 | Sat 15 Aug | 10-0 v Bristol Manor FarmBristol Manor Farm 0-0 Portland United | Southern League - South Division |
| 3 | Mon 31 Aug | 12-0 v ShaftesburyPortland United 2-0 Shaftesbury | Southern League - South Division |
| 4 | Wed 16 Sep | 13-3 v Paulton RoversPaulton Rovers 3-3 Portland United | Southern League - South Division |
| 5 | Sat 19 Sep | 14-1 v Larkhall AthleticPortland United 4-1 Larkhall Athletic | Southern League - South Division |
| 6 | Tue 29 Sep | 11-2 v Falmouth TownPortland United 1-2 Falmouth Town | Southern League - South Division |
| 7 | Sat 3 Oct | 12-1 v BidefordBideford 1-2 Portland United | Southern League - South Division |
| 8 | Wed 7 Oct | 10-1 v SlimbridgeSlimbridge 1-0 Portland United | Southern League - South Division |
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