| 1 | Sat 26 Jul | 101-0 v Nostell Miners WelfareNostell Miners Welfare 0-1 Winterton Rangers | Northern Counties East League Division One |
| 2 | Wed 30 Jul | 154-2 v Club Thorne CollieryWinterton Rangers 4-2 Club Thorne Colliery | Northern Counties East League Cup First Round |
| 3 | Wed 27 Aug | 90-2 v Doncaster CityDoncaster City 2-0 Winterton Rangers | Northern Counties East League Division One |
| 4 | Sat 30 Aug | 111-4 v Goole AFCWinterton Rangers 1-4 Goole AFC | Northern Counties East League Division One |
| 5 | Wed 3 Sep | 150-1 v WakefieldWinterton Rangers 0-1 Wakefield | Northern Counties East League Division One |
| 6 | Sat 6 Sep | 161-4 v Crowle ColtsCrowle Colts 4-1 Winterton Rangers | Northern Counties East League Division One |
| 7 | Sat 13 Sep | 170-1 v Selby TownWinterton Rangers 0-1 Selby Town | Northern Counties East League Division One |
| 8 | Wed 17 Sep | 150-4 v Worsbrough Bridge AthleticWorsbrough Bridge Athletic 4-0 Winterton Rangers | Northern Counties East League Division One |
| 9 | Sat 20 Sep | 173-2 v Appleby FrodinghamWinterton Rangers 3-2 Appleby Frodingham | Northern Counties East League Division One |
| 10 | Sat 27 Sep | 152-1 v Leeds UFCALeeds UFCA 1-2 Winterton Rangers | Northern Counties East League Division One |
| 11 | Sat 4 Oct | 152-4 v Maltby MainMaltby Main 4-2 Winterton Rangers | Northern Counties East League Division One |
| 12 | Wed 15 Oct | 111-9 v Route One RoversRoute One Rovers 9-1 Winterton Rangers | Northern Counties East League Division One |
| 13 | Sat 18 Oct | 92-1 v Glasshoughton WelfareWinterton Rangers 2-1 Glasshoughton Welfare | Northern Counties East League Division One |
| 14 | Wed 22 Oct | 91-1 v Ilkley TownWinterton Rangers 1-1 Ilkley Town | Northern Counties East League Division One |
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