| 1 | Sat 11 Oct | 151-5 v Grantham TownGrantham Town 5-1 Winterton Rangers | Lincolnshire Senior Trophy First Round |
| 2 | Wed 15 Oct | 101-9 v Route One RoversRoute One Rovers 9-1 Winterton Rangers | Northern Counties East League Division One |
| 3 | Sat 18 Oct | 152-1 v Glasshoughton WelfareWinterton Rangers 2-1 Glasshoughton Welfare | Northern Counties East League Division One |
| 4 | Wed 22 Oct | 81-1 v Ilkley TownWinterton Rangers 1-1 Ilkley Town | Northern Counties East League Division One |
| 5 | Sat 25 Oct | 101-4 v Harrogate Railway AthleticHarrogate Railway Athletic 4-1 Winterton Rangers | Northern Counties East League Division One |
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