| 1 | Sat 9 Aug | 12-1 v HartpuryWinchester City 2-1 Hartpury | Southern League - South Division |
| 2 | Tue 12 Aug | 10-1 v Westbury UnitedWestbury United 1-0 Winchester City | Southern League - South Division |
| 3 | Sat 23 Aug | 13-1 v Sporting Club InkberrowWinchester City 3-1 Sporting Club Inkberrow | Southern League - South Division |
| 4 | Mon 25 Aug | 13-1 v Didcot TownDidcot Town 1-3 Winchester City | Southern League - South Division |
| 5 | Sat 13 Sep | 14-0 v Portishead TownWinchester City 4-0 Portishead Town | Southern League - South Division |
| 6 | Sat 27 Sep | 14-0 v Bristol Manor FarmBristol Manor Farm 0-4 Winchester City | Southern League - South Division |
| 7 | Mon 29 Sep | 13-1 v Swindon SupermarineSwindon Supermarine 1-3 Winchester City | Southern League - South Division |
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