| 1 | Sat 9 Aug | 122-1 v HartpuryWinchester City 2-1 Hartpury | Southern League - South Division |
| 2 | Sat 23 Aug | 63-1 v Sporting Club InkberrowWinchester City 3-1 Sporting Club Inkberrow | Southern League - South Division |
| 3 | Mon 25 Aug | 6 3-1 v Didcot TownDidcot Town 1-3 Winchester City | Southern League - South Division |
| 4 | Sat 13 Sep | 24-0 v Portishead TownWinchester City 4-0 Portishead Town | Southern League - South Division |
| 5 | Sat 27 Sep | 24-0 v Bristol Manor FarmBristol Manor Farm 0-4 Winchester City | Southern League - South Division |
| 6 | Mon 29 Sep | 23-1 v Swindon SupermarineSwindon Supermarine 1-3 Winchester City | Southern League - South Division |
| 7 | Sat 11 Oct | 21-4 v Malvern TownMalvern Town 4-1 Winchester City | Southern League - South Division |
| 8 | Tue 14 Oct | 21-1 v Melksham TownWinchester City 1-1 Melksham Town | Southern League - South Division |
| 9 | Sat 18 Oct | 6 1-1 v Frome TownFrome Town 1-1 Winchester City | Southern League - South Division |
| 10 | Sat 25 Oct | 62-2 v Brixham AFCWinchester City 2-2 Brixham AFC | Southern League - South Division |
| 11 | Tue 28 Oct | 61-1 v Bishops CleeveWinchester City 1-1 Bishops Cleeve | Southern League - South Division |
| 12 | Sat 1 Nov | 63-1 v Mousehole AFCMousehole AFC 1-3 Winchester City | Southern League - South Division |
| 13 | Tue 4 Nov | 62-0 v BidefordWinchester City 2-0 Bideford | Southern League - South Division |
| 14 | Wed 12 Nov | 62-1 v Larkhall AthleticLarkhall Athletic 1-2 Winchester City | Southern League - South Division |
| 15 | Sat 15 Nov | 63-1 v Exmouth TownWinchester City 3-1 Exmouth Town | Southern League - South Division |
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