| 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 |
| 6 | Tue 4 Nov | 82-0 v BidefordWinchester City 2-0 Bideford | Southern League - South Division |
| 7 | Sat 8 Nov | 124-2 v Falmouth TownWinchester City 4-2 Falmouth Town | Southern League - South Division |
| 8 | Wed 12 Nov | 42-1 v Larkhall AthleticLarkhall Athletic 1-2 Winchester City | Southern League - South Division |
| 9 | Sat 13 Dec | 16 0-0 v HartpuryHartpury 0-0 Winchester City | Southern League - South Division |
| 10 | Sat 20 Dec | 62-0 v ShaftesburyWinchester City 2-0 Shaftesbury | Southern League - South Division |
| 11 | Sat 27 Dec | 6 2-0 v BashleyBashley 0-2 Winchester City | Southern League - South Division |
| 12 | Sat 10 Jan | 161-3 v Frome TownWinchester City 1-3 Frome Town | Southern League - South Division |
| 13 | Wed 14 Jan | 4 2-1 v TavistockTavistock 1-2 Winchester City | Southern League - South Division |
| 14 | Sat 17 Jan | 4 1-1 v Brixham AFCBrixham AFC 1-1 Winchester City | Southern League - South Division |
| 15 | Sat 24 Jan | 52-2 v Swindon SupermarineWinchester City 2-2 Swindon Supermarine | Southern League - South Division |
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