| 1 | Sat 8 Aug | 95-0 v Egham TownWinchester City 5-0 Egham Town | Isthmian League - South Central Division | 1 |
| 2 | Sat 15 Aug | 94-0 v WestfieldWestfield 0-4 Winchester City | Isthmian League - South Central Division | 1 |
| 3 | Tue 18 Aug | 94-1 v AFC StonehamWinchester City 4-1 AFC Stoneham | Isthmian League - South Central Division | 1 |
| 4 | Sat 3 Oct | 94-2 v Windsor & EtonWinchester City 4-2 Windsor & Eton | Isthmian League - South Central Division | 1 |
| 5 | Tue 6 Oct | 91-5 v MoneyfieldsMoneyfields 5-1 Winchester City | Isthmian League - South Central Division | 1 |
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