| 1 | Sat 27 Sep | 184-0 v Bristol Manor FarmBristol Manor Farm 0-4 Winchester City | Southern League - South Division |
| 2 | Mon 29 Sep | 163-1 v Swindon SupermarineSwindon Supermarine 1-3 Winchester City | Southern League - South Division |
| 3 | Sat 18 Oct | 161-1 v Frome TownFrome Town 1-1 Winchester City | Southern League - South Division |
| 4 | Sat 25 Oct | 32-2 v Brixham AFCWinchester City 2-2 Brixham AFC | Southern League - South Division |
| 5 | Sat 1 Nov | 173-1 v Mousehole AFCMousehole AFC 1-3 Winchester City | Southern League - South Division |
| 6 | Tue 4 Nov | 172-0 v BidefordWinchester City 2-0 Bideford | Southern League - South Division |
| 7 | Sat 8 Nov | 174-2 v Falmouth TownWinchester City 4-2 Falmouth Town | Southern League - South Division |
| 8 | Wed 12 Nov | 162-1 v Larkhall AthleticLarkhall Athletic 1-2 Winchester City | Southern League - South Division |
| 9 | Sat 15 Nov | 163-1 v Exmouth TownWinchester City 3-1 Exmouth Town | Southern League - South Division |
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