| 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 |
| 12 | Sat 1 Nov | 70-3 v Dearne & DistrictWinterton Rangers 0-3 Dearne & District | Northern Counties East League Division One |
| 13 | Sat 8 Nov | 70-2 v Louth TownLouth Town 2-0 Winterton Rangers | Northern Counties East League Division One |
| 14 | Sat 15 Nov | 71-3 v South LeedsWinterton Rangers 1-3 South Leeds | Northern Counties East League Division One |
| 15 | Sat 22 Nov | 153-0 v Nostell Miners WelfareWinterton Rangers 3-0 Nostell Miners Welfare | Northern Counties East League Division One |
| 16 | Wed 26 Nov | 81-6 v Route One RoversWinterton Rangers 1-6 Route One Rovers | Northern Counties East League Cup Third Round |
| 17 | Sat 6 Dec | 143-0 v Athersley RecreationAthersley Recreation 0-3 Winterton Rangers | Northern Counties East League Division One |
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