| 1 | Sat 6 Sep | 141-4 v Crowle ColtsCrowle Colts 4-1 Winterton Rangers | Northern Counties East League Division One |
| 2 | Sat 13 Sep | 70-1 v Selby TownWinterton Rangers 0-1 Selby Town | Northern Counties East League Division One |
| 3 | Wed 17 Sep | 100-4 v Worsbrough Bridge AthleticWorsbrough Bridge Athletic 4-0 Winterton Rangers | Northern Counties East League Division One |
| 4 | Sat 20 Sep | 103-2 v Appleby FrodinghamWinterton Rangers 3-2 Appleby Frodingham | Northern Counties East League Division One |
| 5 | Sat 27 Sep | 102-1 v Leeds UFCALeeds UFCA 1-2 Winterton Rangers | Northern Counties East League Division One |
| 6 | Sat 4 Oct | 102-4 v Maltby MainMaltby Main 4-2 Winterton Rangers | Northern Counties East League Division One |
| 7 | Sat 11 Oct | 101-5 v Grantham TownGrantham Town 5-1 Winterton Rangers | Lincolnshire Senior Trophy First Round |
| 8 | Wed 15 Oct | 71-9 v Route One RoversRoute One Rovers 9-1 Winterton Rangers | Northern Counties East League Division One |
| 9 | Sat 18 Oct | 72-1 v Glasshoughton WelfareWinterton Rangers 2-1 Glasshoughton Welfare | Northern Counties East League Division One |
| 10 | Wed 22 Oct | 111-1 v Ilkley TownWinterton Rangers 1-1 Ilkley Town | Northern Counties East League Division One |
| 11 | Sat 25 Oct | 11 1-4 v Harrogate Railway AthleticHarrogate Railway Athletic 4-1 Winterton Rangers | Northern Counties East League Division One |
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