| 1 | Tue 11 Aug | 141-2 v Westbury UnitedPortland United 1-2 Westbury United | Southern League - South Division |
| 2 | Sat 15 Aug | 140-0 v Bristol Manor FarmBristol Manor Farm 0-0 Portland United | Southern League - South Division |
| 3 | Mon 31 Aug | 22-0 v ShaftesburyPortland United 2-0 Shaftesbury | Southern League - South Division |
| 4 | Sat 19 Sep | 154-1 v Larkhall AthleticPortland United 4-1 Larkhall Athletic | Southern League - South Division |
| 5 | Tue 29 Sep | 151-2 v Falmouth TownPortland United 1-2 Falmouth Town | Southern League - South Division |
| 6 | Sat 3 Oct | 122-1 v BidefordBideford 1-2 Portland United | Southern League - South Division |
| 7 | Wed 7 Oct | 70-1 v SlimbridgeSlimbridge 1-0 Portland United | Southern League - South Division |
| 8 | Sat 10 Oct | 70-4 v Sporting Club InkberrowPortland United 0-4 Sporting Club Inkberrow | Southern League - South Division |
| 9 | Tue 13 Oct | 73-2 v Exmouth TownPortland United 3-2 Exmouth Town | Southern League - South Division |
| 10 | Sat 17 Oct | 154-1 v Tiverton TownTiverton Town 1-4 Portland United | Southern League - South Division |
| 11 | Tue 20 Oct | 20-6 v Melksham TownMelksham Town 6-0 Portland United | Southern League - South Division |
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