| 1 | Tue 11 Aug | 5 1-2 v Westbury UnitedPortland United 1-2 Westbury United | Southern League - South Division |
| 2 | Sat 15 Aug | 50-0 v Bristol Manor FarmBristol Manor Farm 0-0 Portland United | Southern League - South Division |
| 3 | Mon 31 Aug | 52-0 v ShaftesburyPortland United 2-0 Shaftesbury | Southern League - South Division |
| 4 | Wed 16 Sep | 53-3 v Paulton RoversPaulton Rovers 3-3 Portland United | Southern League - South Division |
| 5 | Sat 19 Sep | 54-1 v Larkhall AthleticPortland United 4-1 Larkhall Athletic | Southern League - South Division |
| 6 | Tue 29 Sep | 51-2 v Falmouth TownPortland United 1-2 Falmouth Town | Southern League - South Division |
| 7 | Sat 3 Oct | 5 2-1 v BidefordBideford 1-2 Portland United | Southern League - South Division |
| 8 | Wed 7 Oct | 5 0-1 v SlimbridgeSlimbridge 1-0 Portland United | Southern League - South Division |
| 9 | Sat 10 Oct | 5 0-4 v Sporting Club InkberrowPortland United 0-4 Sporting Club Inkberrow | Southern League - South Division |
| 10 | Tue 13 Oct | 5 3-2 v Exmouth TownPortland United 3-2 Exmouth Town | Southern League - South Division |
| 11 | Sat 17 Oct | 54-1 v Tiverton TownTiverton Town 1-4 Portland United | Southern League - South Division |
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