| 1 | Sat 26 Jul | 141-0 v Nostell Miners WelfareNostell Miners Welfare 0-1 Winterton Rangers | Northern Counties East League Division One |
| 2 | Wed 30 Jul | 24-2 v Club Thorne CollieryWinterton Rangers 4-2 Club Thorne Colliery | Northern Counties East League Cup First Round |
| 3 | Wed 6 Aug | 22-3 v Armthorpe WelfareWinterton Rangers 2-3 Armthorpe Welfare | Northern Counties East League Division One |
| 4 | Sat 9 Aug | 3 0-1 v Club Thorne CollieryClub Thorne Colliery 1-0 Winterton Rangers | Northern Counties East League Division One |
| 5 | Sat 30 Aug | 121-4 v Goole AFCWinterton Rangers 1-4 Goole AFC | Northern Counties East League Division One |
| 6 | Wed 3 Sep | 20-1 v WakefieldWinterton Rangers 0-1 Wakefield | Northern Counties East League Division One |
| 7 | Sat 6 Sep | 21-4 v Crowle ColtsCrowle Colts 4-1 Winterton Rangers | Northern Counties East League Division One |
| 8 | Sat 13 Sep | 20-1 v Selby TownWinterton Rangers 0-1 Selby Town | Northern Counties East League Division One |
| 9 | Wed 17 Sep | 20-4 v Worsbrough Bridge AthleticWorsbrough Bridge Athletic 4-0 Winterton Rangers | Northern Counties East League Division One |
| 10 | Sat 20 Sep | 73-2 v Appleby FrodinghamWinterton Rangers 3-2 Appleby Frodingham | Northern Counties East League Division One |
| 11 | Sat 27 Sep | 2 2-1 v Leeds UFCALeeds UFCA 1-2 Winterton Rangers | Northern Counties East League Division One |
| 12 | Sat 4 Oct | 22-4 v Maltby MainMaltby Main 4-2 Winterton Rangers | Northern Counties East League Division One |
| 13 | Sat 11 Oct | 41-5 v Grantham TownGrantham Town 5-1 Winterton Rangers | Lincolnshire Senior Trophy First Round |
| 14 | Wed 15 Oct | 21-9 v Route One RoversRoute One Rovers 9-1 Winterton Rangers | Northern Counties East League Division One |
| 15 | Sat 18 Oct | 22-1 v Glasshoughton WelfareWinterton Rangers 2-1 Glasshoughton Welfare | Northern Counties East League Division One |
| 16 | Wed 22 Oct | 21-1 v Ilkley TownWinterton Rangers 1-1 Ilkley Town | Northern Counties East League Division One |
| 17 | Sat 25 Oct | 21-4 v Harrogate Railway AthleticHarrogate Railway Athletic 4-1 Winterton Rangers | Northern Counties East League Division One |
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