| 1 | Wed 17 Sep | 40-4 v Worsbrough Bridge AthleticWorsbrough Bridge Athletic 4-0 Winterton Rangers | Northern Counties East League Division One |
| 2 | Sat 20 Sep | 43-2 v Appleby FrodinghamWinterton Rangers 3-2 Appleby Frodingham | Northern Counties East League Division One |
| 3 | Sat 27 Sep | 62-1 v Leeds UFCALeeds UFCA 1-2 Winterton Rangers | Northern Counties East League Division One |
| 4 | Sat 4 Oct | 62-4 v Maltby MainMaltby Main 4-2 Winterton Rangers | Northern Counties East League Division One |
| 5 | Sat 11 Oct | 61-5 v Grantham TownGrantham Town 5-1 Winterton Rangers | Lincolnshire Senior Trophy First Round |
| 6 | Wed 15 Oct | 61-9 v Route One RoversRoute One Rovers 9-1 Winterton Rangers | Northern Counties East League Division One |
| 7 | Sat 18 Oct | 62-1 v Glasshoughton WelfareWinterton Rangers 2-1 Glasshoughton Welfare | Northern Counties East League Division One |
| 8 | Wed 22 Oct | 61-1 v Ilkley TownWinterton Rangers 1-1 Ilkley Town | Northern Counties East League Division One |
| 9 | Sat 25 Oct | 51-4 v Harrogate Railway AthleticHarrogate Railway Athletic 4-1 Winterton Rangers | Northern Counties East League Division One |
| 10 | Sat 1 Nov | 50-3 v Dearne & DistrictWinterton Rangers 0-3 Dearne & District | Northern Counties East League Division One |
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