| 1 | Sat 9 Aug | 12-1 v HartpuryWinchester City 2-1 Hartpury | Southern League - South Division |
| 2 | Tue 12 Aug | 10-1 v Westbury UnitedWestbury United 1-0 Winchester City | Southern League - South Division |
| 3 | Sat 23 Aug | 13-1 v Sporting Club InkberrowWinchester City 3-1 Sporting Club Inkberrow | Southern League - South Division |
| 4 | Mon 25 Aug | 13-1 v Didcot TownDidcot Town 1-3 Winchester City | Southern League - South Division |
| 5 | Sat 13 Sep | 14-0 v Portishead TownWinchester City 4-0 Portishead Town | Southern League - South Division |
| 6 | Sat 27 Sep | 14-0 v Bristol Manor FarmBristol Manor Farm 0-4 Winchester City | Southern League - South Division |
| 7 | Mon 29 Sep | 13-1 v Swindon SupermarineSwindon Supermarine 1-3 Winchester City | Southern League - South Division |
| 8 | Sat 11 Oct | 11-4 v Malvern TownMalvern Town 4-1 Winchester City | Southern League - South Division |
| 9 | Tue 14 Oct | 11-1 v Melksham TownWinchester City 1-1 Melksham Town | Southern League - South Division |
| 10 | Sat 18 Oct | 11-1 v Frome TownFrome Town 1-1 Winchester City | Southern League - South Division |
| 11 | Sat 25 Oct | 12-2 v Brixham AFCWinchester City 2-2 Brixham AFC | Southern League - South Division |
| 12 | Tue 28 Oct | 11-1 v Bishops CleeveWinchester City 1-1 Bishops Cleeve | Southern League - South Division |
| 13 | Sat 1 Nov | 1 3-1 v Mousehole AFCMousehole AFC 1-3 Winchester City | Southern League - South Division |
| 14 | Tue 4 Nov | 12-0 v BidefordWinchester City 2-0 Bideford | Southern League - South Division |
| 15 | Sat 8 Nov | 14-2 v Falmouth TownWinchester City 4-2 Falmouth Town | Southern League - South Division |
| 16 | Wed 12 Nov | 12-1 v Larkhall AthleticLarkhall Athletic 1-2 Winchester City | Southern League - South Division |
| 17 | Sat 15 Nov | 1 3-1 v Exmouth TownWinchester City 3-1 Exmouth Town | Southern League - South Division |
| 18 | Sat 22 Nov | 12-3 v Portishead TownPortishead Town 3-2 Winchester City | Southern League - South Division |
| 19 | Tue 25 Nov | 13-0 v Westbury UnitedWinchester City 3-0 Westbury United | Southern League - South Division |
| 20 | Sat 6 Dec | 12-1 v Willand RoversWinchester City 2-1 Willand Rovers | Southern League - South Division |
| 21 | Sat 13 Dec | 10-0 v HartpuryHartpury 0-0 Winchester City | Southern League - South Division |
| 22 | Sat 20 Dec | 12-0 v ShaftesburyWinchester City 2-0 Shaftesbury | Southern League - South Division |
| 23 | Sat 27 Dec | 12-0 v BashleyBashley 0-2 Winchester City | Southern League - South Division |
| 24 | Sat 3 Jan | 12-0 v Didcot TownWinchester City 2-0 Didcot Town | Southern League - South Division |
| 25 | Sat 10 Jan | 11-3 v Frome TownWinchester City 1-3 Frome Town | Southern League - South Division |
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