| 1 | Sat 23 Aug | 93-1 v Sporting Club InkberrowWinchester City 3-1 Sporting Club Inkberrow | Southern League - South Division | 1 |
| 2 | Mon 25 Aug | 103-1 v Didcot TownDidcot Town 1-3 Winchester City | Southern League - South Division | 1 |
| 3 | Sat 27 Sep | 94-0 v Bristol Manor FarmBristol Manor Farm 0-4 Winchester City | Southern League - South Division | 2 |
| 4 | Sat 11 Oct | 91-4 v Malvern TownMalvern Town 4-1 Winchester City | Southern League - South Division | 1 |
| 5 | Sat 25 Oct | 92-2 v Brixham AFCWinchester City 2-2 Brixham AFC | Southern League - South Division | 1 |
| 6 | Sat 1 Nov | 183-1 v Mousehole AFCMousehole AFC 1-3 Winchester City | Southern League - South Division | 1 |
| 7 | Tue 25 Nov | 93-0 v Westbury UnitedWinchester City 3-0 Westbury United | Southern League - South Division | 1 |
| 8 | Sat 6 Dec | 92-1 v Willand RoversWinchester City 2-1 Willand Rovers | Southern League - South Division | 1 |
| 9 | Sat 28 Feb | 173-2 v Mousehole AFCWinchester City 3-2 Mousehole AFC | Southern League - South Division | 1 |
| 10 | Sat 7 Mar | 146-5 v Falmouth TownFalmouth Town 5-6 Winchester City | Southern League - South Division | 2 |
| 11 | Tue 17 Mar | 96-1 v BidefordBideford 1-6 Winchester City | Southern League - South Division | 1 |
| 12 | Sat 28 Mar | 106-1 v TavistockWinchester City 6-1 Tavistock | Southern League - South Division | 1 |
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