| 1 | Sat 13 Sep | 104-0 v Portishead TownWinchester City 4-0 Portishead Town | Southern League - South Division |
| 2 | Sat 27 Sep | 104-0 v Bristol Manor FarmBristol Manor Farm 0-4 Winchester City | Southern League - South Division |
| 3 | Mon 29 Sep | 103-1 v Swindon SupermarineSwindon Supermarine 1-3 Winchester City | Southern League - South Division |
| 4 | Sat 11 Oct | 101-4 v Malvern TownMalvern Town 4-1 Winchester City | Southern League - South Division |
| 5 | Tue 14 Oct | 101-1 v Melksham TownWinchester City 1-1 Melksham Town | Southern League - South Division |
| 6 | Sat 18 Oct | 101-1 v Frome TownFrome Town 1-1 Winchester City | Southern League - South Division |
| 7 | Sat 25 Oct | 102-2 v Brixham AFCWinchester City 2-2 Brixham AFC | Southern League - South Division |
| 8 | Tue 28 Oct | 101-1 v Bishops CleeveWinchester City 1-1 Bishops Cleeve | Southern League - South Division |
Football Web Pages