| 1 | Sat 9 Aug | 32-1 v HartpuryWinchester City 2-1 Hartpury | Southern League - South Division |
| 2 | Tue 12 Aug | 30-1 v Westbury UnitedWestbury United 1-0 Winchester City | Southern League - South Division |
| 3 | Sat 23 Aug | 33-1 v Sporting Club InkberrowWinchester City 3-1 Sporting Club Inkberrow | Southern League - South Division |
| 4 | Mon 25 Aug | 33-1 v Didcot TownDidcot Town 1-3 Winchester City | Southern League - South Division |
| 5 | Sat 13 Sep | 34-0 v Portishead TownWinchester City 4-0 Portishead Town | Southern League - South Division |
| 6 | Sat 27 Sep | 34-0 v Bristol Manor FarmBristol Manor Farm 0-4 Winchester City | Southern League - South Division |
| 7 | Mon 29 Sep | 3 3-1 v Swindon SupermarineSwindon Supermarine 1-3 Winchester City | Southern League - South Division |
| 8 | Sat 11 Oct | 31-4 v Malvern TownMalvern Town 4-1 Winchester City | Southern League - South Division |
| 9 | Tue 14 Oct | 3 1-1 v Melksham TownWinchester City 1-1 Melksham Town | Southern League - South Division |
| 10 | Sat 18 Oct | 31-1 v Frome TownFrome Town 1-1 Winchester City | Southern League - South Division |
| 11 | Sat 10 Jan | 171-3 v Frome TownWinchester City 1-3 Frome Town | Southern League - South Division |
| 12 | Wed 14 Jan | 172-1 v TavistockTavistock 1-2 Winchester City | Southern League - South Division |
| 13 | Sat 17 Jan | 161-1 v Brixham AFCBrixham AFC 1-1 Winchester City | Southern League - South Division |
| 14 | Sat 24 Jan | 3 2-2 v Swindon SupermarineWinchester City 2-2 Swindon Supermarine | Southern League - South Division |
| 15 | Sat 7 Feb | 31-1 v Malvern TownWinchester City 1-1 Malvern Town | Southern League - South Division |
| 16 | Sat 14 Feb | 30-1 v Melksham TownMelksham Town 1-0 Winchester City | Southern League - South Division |
| 17 | Sat 28 Feb | 33-2 v Mousehole AFCWinchester City 3-2 Mousehole AFC | Southern League - South Division |
| 18 | Sat 7 Mar | 176-5 v Falmouth TownFalmouth Town 5-6 Winchester City | Southern League - South Division |
| 19 | Sat 14 Mar | 30-2 v Larkhall AthleticWinchester City 0-2 Larkhall Athletic | Southern League - South Division |
| 20 | Tue 17 Mar | 15 6-1 v BidefordBideford 1-6 Winchester City | Southern League - South Division |
| 21 | Sat 21 Mar | 162-2 v Sporting Club InkberrowSporting Club Inkberrow 2-2 Winchester City | Southern League - South Division |
| 22 | Fri 3 Apr | 3 1-0 v Willand RoversWilland Rovers 0-1 Winchester City | Southern League - South Division |
| 23 | Sat 11 Apr | 161-2 v ShaftesburyShaftesbury 2-1 Winchester City | Southern League - South Division |
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