| 1 | Sat 8 Aug | 55-0 v Egham TownWinchester City 5-0 Egham Town | Isthmian League - South Central Division |
| 2 | Sat 15 Aug | 54-0 v WestfieldWestfield 0-4 Winchester City | Isthmian League - South Central Division |
| 3 | Tue 18 Aug | 54-1 v AFC StonehamWinchester City 4-1 AFC Stoneham | Isthmian League - South Central Division |
| 4 | Tue 1 Sep | 171-1 v Littlehampton TownLittlehampton Town 1-1 Winchester City | Isthmian League - South Central Division |
| 5 | Sat 5 Sep | 6 1-1 v Bedfont SportsWinchester City 1-1 Bedfont Sports | Isthmian League - South Central Division |
| 6 | Sat 19 Sep | 120-0 v Jersey BullsWinchester City 0-0 Jersey Bulls | Isthmian League - South Central Division |
| 7 | Tue 22 Sep | 121-2 v Bognor Regis TownWinchester City 1-2 Bognor Regis Town | Isthmian League - South Central Division |
| 8 | Sat 26 Sep | 5 1-2 v Raynes Park ValeRaynes Park Vale 2-1 Winchester City | Isthmian League - South Central Division |
| 9 | Sat 3 Oct | 124-2 v Windsor & EtonWinchester City 4-2 Windsor & Eton | Isthmian League - South Central Division |
| 10 | Tue 6 Oct | 121-5 v MoneyfieldsMoneyfields 5-1 Winchester City | Isthmian League - South Central Division |
| 11 | Sat 10 Oct | 3 3-2 v SouthallWinchester City 3-2 Southall | Isthmian League - South Central Division |
| 12 | Sat 17 Oct | 34-2 v HendonHendon 2-4 Winchester City | Isthmian League - South Central Division |
| 13 | Tue 20 Oct | 34-1 v AFC StonehamAFC Stoneham 1-4 Winchester City | Isthmian League - South Central Division |
| 14 | Sat 24 Oct | 34-2 v CobhamWinchester City 4-2 Cobham | Isthmian League - South Central Division |
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