| 1 | Sat 8 Aug | 15-0 v Egham TownWinchester City 5-0 Egham Town | Isthmian League - South Central Division |
| 2 | Sat 15 Aug | 14-0 v WestfieldWestfield 0-4 Winchester City | Isthmian League - South Central Division |
| 3 | Tue 18 Aug | 14-1 v AFC StonehamWinchester City 4-1 AFC Stoneham | Isthmian League - South Central Division |
| 4 | Tue 1 Sep | 11-1 v Littlehampton TownLittlehampton Town 1-1 Winchester City | Isthmian League - South Central Division |
| 5 | Sat 5 Sep | 11-1 v Bedfont SportsWinchester City 1-1 Bedfont Sports | Isthmian League - South Central Division |
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