| 1 | Mon 25 Aug | 43-1 v Didcot TownDidcot Town 1-3 Winchester City | Southern League - South Division |
| 2 | Sat 27 Sep | 84-0 v Bristol Manor FarmBristol Manor Farm 0-4 Winchester City | Southern League - South Division |
| 3 | Mon 29 Sep | 8 3-1 v Swindon SupermarineSwindon Supermarine 1-3 Winchester City | Southern League - South Division |
| 4 | Sat 25 Oct | 15 2-2 v Brixham AFCWinchester City 2-2 Brixham AFC | Southern League - South Division |
| 5 | Tue 28 Oct | 8 1-1 v Bishops CleeveWinchester City 1-1 Bishops Cleeve | Southern League - South Division |
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