| 1 | Sat 1 Aug | 160-1 v Hemsworth Miners WelfareHemsworth Miners Welfare 1-0 Winterton Rangers | Northern Counties East League Division One |
| 2 | Wed 5 Aug | 93-0 v Immingham TownWinterton Rangers 3-0 Immingham Town | Northern Counties East League Division One |
| 3 | Sat 8 Aug | 94-3 v Harrogate Railway AthleticHarrogate Railway Athletic 3-4 Winterton Rangers | Northern Counties East League Division One |
| 4 | Sat 15 Aug | 91-2 v AFC DarwenWinterton Rangers 1-2 AFC Darwen | FA Vase First Qualifying Round |
| 5 | Wed 19 Aug | 91-5 v Club Thorne CollieryWinterton Rangers 1-5 Club Thorne Colliery | Northern Counties East League Division One |
| 6 | Sat 5 Sep | 92-1 v Leeds UFCAWinterton Rangers 2-1 Leeds UFCA | Northern Counties East League Division One |
| 7 | Sat 12 Sep | 93-1 v Armthorpe WelfareWinterton Rangers 3-1 Armthorpe Welfare | Northern Counties East League Division One |
| 8 | Tue 15 Sep | 90-3 v Goole AFCGoole AFC 3-0 Winterton Rangers | Northern Counties East League Division One |
| 9 | Sat 19 Sep | 92-2 v Ilkley TownWinterton Rangers 2-2 Ilkley Town | Northern Counties East League Division One |
| 10 | Sat 26 Sep | 92-4 v Brigg TownBrigg Town 4-2 Winterton Rangers | Northern Counties East League Division One |
| 11 | Wed 30 Sep | 92-0 v Kinsley BoysWinterton Rangers 2-0 Kinsley Boys | Northern Counties East League Division One |
| 12 | Sat 3 Oct | 92-1 v Selby TownSelby Town 1-2 Winterton Rangers | Northern Counties East League Division One |
| 13 | Sat 10 Oct | 92-3 v Route One RoversWinterton Rangers 2-3 Route One Rovers | Northern Counties East League Division One |
| 14 | Sat 17 Oct | 95-0 v Athersley RecreationAthersley Recreation 0-5 Winterton Rangers | Northern Counties East League Division One |
| 15 | Sat 24 Oct | 92-3 v Crowle ColtsWinterton Rangers 2-3 Crowle Colts | Northern Counties East League Division One |
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