| 1 | Sat 1 Aug | 20-1 v Hemsworth Miners WelfareHemsworth Miners Welfare 1-0 Winterton Rangers | Northern Counties East League Division One |
| 2 | Wed 5 Aug | 23-0 v Immingham TownWinterton Rangers 3-0 Immingham Town | Northern Counties East League Division One |
| 3 | Sat 8 Aug | 24-3 v Harrogate Railway AthleticHarrogate Railway Athletic 3-4 Winterton Rangers | Northern Counties East League Division One |
| 4 | Wed 12 Aug | 21-2 v Harrogate Railway AthleticWinterton Rangers 1-2 Harrogate Railway Athletic | Northern Counties East League Cup First Round |
| 5 | Sat 15 Aug | 2 1-2 v AFC DarwenWinterton Rangers 1-2 AFC Darwen | FA Vase First Qualifying Round |
| 6 | Wed 19 Aug | 121-5 v Club Thorne CollieryWinterton Rangers 1-5 Club Thorne Colliery | Northern Counties East League Division One |
| 7 | Wed 26 Aug | 22-1 v South LeedsWinterton Rangers 2-1 South Leeds | Northern Counties East League Division One |
| 8 | Sat 5 Sep | 32-1 v Leeds UFCAWinterton Rangers 2-1 Leeds UFCA | Northern Counties East League Division One |
| 9 | Sat 12 Sep | 23-1 v Armthorpe WelfareWinterton Rangers 3-1 Armthorpe Welfare | Northern Counties East League Division One |
| 10 | Tue 15 Sep | 20-3 v Goole AFCGoole AFC 3-0 Winterton Rangers | Northern Counties East League Division One |
| 11 | Sat 19 Sep | 22-2 v Ilkley TownWinterton Rangers 2-2 Ilkley Town | Northern Counties East League Division One |
| 12 | Sat 26 Sep | 22-4 v Brigg TownBrigg Town 4-2 Winterton Rangers | Northern Counties East League Division One |
| 13 | Wed 30 Sep | 22-0 v Kinsley BoysWinterton Rangers 2-0 Kinsley Boys | Northern Counties East League Division One |
| 14 | Sat 3 Oct | 22-1 v Selby TownSelby Town 1-2 Winterton Rangers | Northern Counties East League Division One |
| 15 | Sat 10 Oct | 22-3 v Route One RoversWinterton Rangers 2-3 Route One Rovers | Northern Counties East League Division One |
| 16 | Wed 14 Oct | 21-5 v Appleby FrodinghamWinterton Rangers 1-5 Appleby Frodingham | Lincolnshire Senior Trophy First Round |
| 17 | Sat 17 Oct | 25-0 v Athersley RecreationAthersley Recreation 0-5 Winterton Rangers | Northern Counties East League Division One |
| 18 | Sat 24 Oct | 22-3 v Crowle ColtsWinterton Rangers 2-3 Crowle Colts | Northern Counties East League Division One |
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