| 1 | Sat 12 Aug 2017 | 14-2 v Shortwood UnitedShortwood United 2-4 Winchester City | Evo-Stik South West |
| 2 | Tue 15 Aug 2017 | 10-1 v KidlingtonWinchester City 0-1 Kidlington | Evo-Stik South West |
| 3 | Sat 19 Aug 2017 | 14-0 v Bracknell TownBracknell Town 0-4 Winchester City | Emirates FA Cup Preliminary Round |
| 4 | Sat 26 Aug 2017 | 12-1 v Larkhall AthleticLarkhall Athletic 1-2 Winchester City | Evo-Stik South West |
| 5 | Mon 28 Aug 2017 | 11-0 v Wimborne TownWinchester City 1-0 Wimborne Town | Evo-Stik South West |
| 6 | Sat 2 Sep 2017 | 10-1 v Paulton RoversPaulton Rovers 1-0 Winchester City | Emirates FA Cup First Qualifying Round |
| 7 | Sat 9 Sep 2017 | 10-1 v Cirencester TownCirencester Town 1-0 Winchester City | Evo-Stik South West |
| 8 | Sat 23 Sep 2017 | 13-0 v Mangotsfield UnitedWinchester City 3-0 Mangotsfield United | Evo-Stik South West |
| 9 | Tue 26 Sep 2017 | 14-2 v Didcot TownDidcot Town 2-4 Winchester City | Evo-Stik South West |
| 10 | Sat 30 Sep 2017 | 14-1 v Barnstaple TownBarnstaple Town 1-4 Winchester City | Evo-Stik South West |
| 11 | Sat 7 Oct 2017 | 11-3 v KidlingtonKidlington 3-1 Winchester City | Buildbase FA Trophy Preliminary Round |
| 12 | Sat 14 Oct 2017 | 11-2 v Bristol Manor FarmWinchester City 1-2 Bristol Manor Farm | Evo-Stik South West |
| 13 | Tue 17 Oct 2017 | 11-1 v Paulton RoversWinchester City 1-1 Paulton Rovers | Evo-Stik South West |
| 14 | Sat 21 Oct 2017 | 11-4 v Taunton TownTaunton Town 4-1 Winchester City | Evo-Stik South West |
| 15 | Fri 27 Oct 2017 | 14-5 v SalisburyWinchester City 4-5 Salisbury | Evo-Stik South West |
| 16 | Sat 4 Nov 2017 | 12-2 v Cinderford TownCinderford Town 2-2 Winchester City | Evo-Stik South West |
| 17 | Sat 11 Nov 2017 | 12-1 v Bishops CleeveWinchester City 2-1 Bishops Cleeve | Evo-Stik South West |
| 18 | Sat 18 Nov 2017 | 11-1 v Yate TownYate Town 1-1 Winchester City | Evo-Stik South West |
| 19 | Tue 21 Nov 2017 | 13-2 v Swindon SupermarineWinchester City 3-2 Swindon Supermarine | Evo-Stik South West |
| 20 | Sat 25 Nov 2017 | 12-3 v BidefordWinchester City 2-3 Bideford | Evo-Stik South West |
| 21 | Tue 28 Nov 2017 | 12-1 v North LeighNorth Leigh 1-2 Winchester City | Evo-Stik South West |
| 22 | Sat 2 Dec 2017 | 12-0 v Evesham UnitedWinchester City 2-0 Evesham United | Evo-Stik South West |
| 23 | Sat 23 Dec 2017 | 15-1 v Shortwood UnitedWinchester City 5-1 Shortwood United | Evo-Stik South West |
| 24 | Tue 26 Dec 2017 | 10-3 v Wimborne TownWimborne Town 3-0 Winchester City | Evo-Stik South West |
| 25 | Mon 1 Jan 2018 | 11-1 v AFC TottonWinchester City 1-1 AFC Totton | Evo-Stik South West |
| 26 | Sat 6 Jan 2018 | 12-2 v Paulton RoversPaulton Rovers 2-2 Winchester City | Evo-Stik South West |
| 27 | Sat 13 Jan 2018 | 13-1 v Larkhall AthleticWinchester City 3-1 Larkhall Athletic | Evo-Stik South West |
| 28 | Wed 17 Jan 2018 | 10-2 v SlimbridgeSlimbridge 2-0 Winchester City | Evo-Stik South West |
| 29 | Sat 27 Jan 2018 | 12-0 v Cinderford TownWinchester City 2-0 Cinderford Town | Evo-Stik South West |
| 30 | Wed 31 Jan 2018 | 11-1 v KidlingtonKidlington 1-1 Winchester City | Evo-Stik South West |
| 31 | Sat 3 Feb 2018 | 11-1 v Mangotsfield UnitedMangotsfield United 1-1 Winchester City | Evo-Stik South West |
| 32 | Sat 10 Feb 2018 | 12-0 v Didcot TownWinchester City 2-0 Didcot Town | Evo-Stik South West |
| 33 | Sat 17 Feb 2018 | 11-4 v Bristol Manor FarmBristol Manor Farm 4-1 Winchester City | Evo-Stik South West |
| 34 | Tue 20 Feb 2018 | 12-4 v Bishops CleeveBishops Cleeve 4-2 Winchester City | Evo-Stik South West |
| 35 | Sat 24 Feb 2018 | 11-1 v Barnstaple TownWinchester City 1-1 Barnstaple Town | Evo-Stik South West |
| 36 | Sat 17 Mar 2018 | 13-0 v SlimbridgeWinchester City 3-0 Slimbridge | Evo-Stik South West |
| 37 | Sat 24 Mar 2018 | 10-1 v Evesham UnitedEvesham United 1-0 Winchester City | Evo-Stik South West |
| 38 | Sat 7 Apr 2018 | 14-1 v Yate TownWinchester City 4-1 Yate Town | Evo-Stik South West |
| 39 | Tue 10 Apr 2018 | 12-2 v SalisburySalisbury 2-2 Winchester City | Evo-Stik South West |
| 40 | Thu 12 Apr 2018 | 10-1 v AFC TottonAFC Totton 1-0 Winchester City | Evo-Stik South West |
| 41 | Sat 14 Apr 2018 | 11-1 v Swindon SupermarineSwindon Supermarine 1-1 Winchester City | Evo-Stik South West |
| 42 | Tue 17 Apr 2018 | 10-5 v Taunton TownWinchester City 0-5 Taunton Town | Evo-Stik South West |
| 43 | Sat 21 Apr 2018 | 12-0 v North LeighWinchester City 2-0 North Leigh | Evo-Stik South West |
| 44 | Tue 24 Apr 2018 | 11-2 v Cirencester TownWinchester City 1-2 Cirencester Town | Evo-Stik South West |
| 45 | Sat 28 Apr 2018 | 10-2 v BidefordBideford 2-0 Winchester City | Evo-Stik South West |
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