| 1 | Sat 9 Aug | 82-1 v HartpuryWinchester City 2-1 Hartpury | Southern League - South Division |
| 2 | Tue 12 Aug | 10 0-1 v Westbury UnitedWestbury United 1-0 Winchester City | Southern League - South Division |
| 3 | Sat 23 Aug | 4 3-1 v Sporting Club InkberrowWinchester City 3-1 Sporting Club Inkberrow | Southern League - South Division |
| 4 | Mon 25 Aug | 83-1 v Didcot TownDidcot Town 1-3 Winchester City | Southern League - South Division |
| 5 | Sat 13 Sep | 84-0 v Portishead TownWinchester City 4-0 Portishead Town | Southern League - South Division |
| 6 | Sat 22 Nov | 182-3 v Portishead TownPortishead Town 3-2 Winchester City | Southern League - South Division |
| 7 | Tue 25 Nov | 163-0 v Westbury UnitedWinchester City 3-0 Westbury United | Southern League - South Division |
| 8 | Sat 6 Dec | 162-1 v Willand RoversWinchester City 2-1 Willand Rovers | Southern League - South Division |
| 9 | Sat 13 Dec | 60-0 v HartpuryHartpury 0-0 Winchester City | Southern League - South Division |
| 10 | Sat 20 Dec | 82-0 v ShaftesburyWinchester City 2-0 Shaftesbury | Southern League - South Division |
| 11 | Sat 27 Dec | 82-0 v BashleyBashley 0-2 Winchester City | Southern League - South Division |
| 12 | Sat 3 Jan | 82-0 v Didcot TownWinchester City 2-0 Didcot Town | Southern League - South Division |
| 13 | Sat 10 Jan | 41-3 v Frome TownWinchester City 1-3 Frome Town | Southern League - South Division |
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