| 1 | Sat 13 Sep | 10-1 v Selby TownWinterton Rangers 0-1 Selby Town | Northern Counties East League Division One |
| 2 | Wed 17 Sep | 10-4 v Worsbrough Bridge AthleticWorsbrough Bridge Athletic 4-0 Winterton Rangers | Northern Counties East League Division One |
| 3 | Sat 20 Sep | 13-2 v Appleby FrodinghamWinterton Rangers 3-2 Appleby Frodingham | Northern Counties East League Division One |
| 4 | Sat 27 Sep | 12-1 v Leeds UFCALeeds UFCA 1-2 Winterton Rangers | Northern Counties East League Division One |
| 5 | Sat 4 Oct | 12-4 v Maltby MainMaltby Main 4-2 Winterton Rangers | Northern Counties East League Division One |
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