| 1 | Sat 25 Oct | 162-2 v Brixham AFCWinchester City 2-2 Brixham AFC | Southern League - South Division |
| 2 | Tue 28 Oct | 91-1 v Bishops CleeveWinchester City 1-1 Bishops Cleeve | Southern League - South Division |
| 3 | Sat 1 Nov | 9 3-1 v Mousehole AFCMousehole AFC 1-3 Winchester City | Southern League - South Division |
| 4 | Tue 4 Nov | 92-0 v BidefordWinchester City 2-0 Bideford | Southern League - South Division |
| 5 | Sat 8 Nov | 94-2 v Falmouth TownWinchester City 4-2 Falmouth Town | Southern League - South Division |
| 6 | Wed 12 Nov | 9 2-1 v Larkhall AthleticLarkhall Athletic 1-2 Winchester City | Southern League - South Division |
| 7 | Sat 15 Nov | 123-1 v Exmouth TownWinchester City 3-1 Exmouth Town | Southern League - South Division |
| 8 | Sat 22 Nov | 92-3 v Portishead TownPortishead Town 3-2 Winchester City | Southern League - South Division |
| 9 | Tue 25 Nov | 123-0 v Westbury UnitedWinchester City 3-0 Westbury United | Southern League - South Division |
| 10 | Sat 6 Dec | 122-1 v Willand RoversWinchester City 2-1 Willand Rovers | Southern League - South Division |
| 11 | Sat 13 Dec | 80-0 v HartpuryHartpury 0-0 Winchester City | Southern League - South Division |
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