| 1 | Sat 20 Dec | 122-0 v ShaftesburyWinchester City 2-0 Shaftesbury | Southern League - South Division |
| 2 | Sat 27 Dec | 18 2-0 v BashleyBashley 0-2 Winchester City | Southern League - South Division |
| 3 | Sat 3 Jan | 6 2-0 v Didcot TownWinchester City 2-0 Didcot Town | Southern League - South Division |
| 4 | Sat 10 Jan | 61-3 v Frome TownWinchester City 1-3 Frome Town | Southern League - South Division |
| 5 | Wed 14 Jan | 62-1 v TavistockTavistock 1-2 Winchester City | Southern League - South Division |
| 6 | Sat 17 Jan | 6 1-1 v Brixham AFCBrixham AFC 1-1 Winchester City | Southern League - South Division |
| 7 | Sat 24 Jan | 62-2 v Swindon SupermarineWinchester City 2-2 Swindon Supermarine | Southern League - South Division |
| 8 | Sat 7 Feb | 121-1 v Malvern TownWinchester City 1-1 Malvern Town | Southern League - South Division |
| 9 | Sat 14 Feb | 150-1 v Melksham TownMelksham Town 1-0 Winchester City | Southern League - South Division |
| 10 | Sat 7 Mar | 56-5 v Falmouth TownFalmouth Town 5-6 Winchester City | Southern League - South Division |
| 11 | Tue 17 Mar | 146-1 v BidefordBideford 1-6 Winchester City | Southern League - South Division |
| 12 | Fri 3 Apr | 161-0 v Willand RoversWilland Rovers 0-1 Winchester City | Southern League - South Division |
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