| 1 | Sat 12 Aug 2017 | 54-2 v Shortwood UnitedShortwood United 2-4 Winchester City | Evo-Stik South West |
| 2 | Tue 15 Aug 2017 | 50-1 v KidlingtonWinchester City 0-1 Kidlington | Evo-Stik South West |
| 3 | Sat 19 Aug 2017 | 54-0 v Bracknell TownBracknell Town 0-4 Winchester City | Emirates FA Cup Preliminary Round |
| 4 | Sat 26 Aug 2017 | 52-1 v Larkhall AthleticLarkhall Athletic 1-2 Winchester City | Evo-Stik South West |
| 5 | Mon 28 Aug 2017 | 51-0 v Wimborne TownWinchester City 1-0 Wimborne Town | Evo-Stik South West |
| 6 | Sat 2 Sep 2017 | 50-1 v Paulton RoversPaulton Rovers 1-0 Winchester City | Emirates FA Cup First Qualifying Round |
| 7 | Sat 9 Sep 2017 | 50-1 v Cirencester TownCirencester Town 1-0 Winchester City | Evo-Stik South West |
| 8 | Sat 23 Sep 2017 | 53-0 v Mangotsfield UnitedWinchester City 3-0 Mangotsfield United | Evo-Stik South West |
| 9 | Tue 26 Sep 2017 | 54-2 v Didcot TownDidcot Town 2-4 Winchester City | Evo-Stik South West |
| 10 | Sat 30 Sep 2017 | 54-1 v Barnstaple TownBarnstaple Town 1-4 Winchester City | Evo-Stik South West |
| 11 | Sat 7 Oct 2017 | 51-3 v KidlingtonKidlington 3-1 Winchester City | Buildbase FA Trophy Preliminary Round |
| 12 | Sat 14 Oct 2017 | 51-2 v Bristol Manor FarmWinchester City 1-2 Bristol Manor Farm | Evo-Stik South West |
| 13 | Tue 17 Oct 2017 | 51-1 v Paulton RoversWinchester City 1-1 Paulton Rovers | Evo-Stik South West |
| 14 | Sat 21 Oct 2017 | 51-4 v Taunton TownTaunton Town 4-1 Winchester City | Evo-Stik South West |
| 15 | Sat 11 Nov 2017 | 52-1 v Bishops CleeveWinchester City 2-1 Bishops Cleeve | Evo-Stik South West |
| 16 | Sat 18 Nov 2017 | 51-1 v Yate TownYate Town 1-1 Winchester City | Evo-Stik South West |
| 17 | Tue 21 Nov 2017 | 5 3-2 v Swindon SupermarineWinchester City 3-2 Swindon Supermarine | Evo-Stik South West |
| 18 | Sat 25 Nov 2017 | 52-3 v BidefordWinchester City 2-3 Bideford | Evo-Stik South West |
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