| 1 | Sat 25 Jul | 30-1 v WakefieldWinterton Rangers 0-1 Wakefield | Northern Counties East League Division One |
| 2 | Sat 1 Aug | 30-1 v Hemsworth Miners WelfareHemsworth Miners Welfare 1-0 Winterton Rangers | Northern Counties East League Division One |
| 3 | Wed 5 Aug | 33-0 v Immingham TownWinterton Rangers 3-0 Immingham Town | Northern Counties East League Division One |
| 4 | Sat 8 Aug | 34-3 v Harrogate Railway AthleticHarrogate Railway Athletic 3-4 Winterton Rangers | Northern Counties East League Division One |
| 5 | Wed 12 Aug | 121-2 v Harrogate Railway AthleticWinterton Rangers 1-2 Harrogate Railway Athletic | Northern Counties East League Cup First Round |
| 6 | Sat 15 Aug | 31-2 v AFC DarwenWinterton Rangers 1-2 AFC Darwen | FA Vase First Qualifying Round |
| 7 | Wed 19 Aug | 31-5 v Club Thorne CollieryWinterton Rangers 1-5 Club Thorne Colliery | Northern Counties East League Division One |
| 8 | Wed 26 Aug | 122-1 v South LeedsWinterton Rangers 2-1 South Leeds | Northern Counties East League Division One |
| 9 | Sat 19 Sep | 32-2 v Ilkley TownWinterton Rangers 2-2 Ilkley Town | Northern Counties East League Division One |
| 10 | Sat 26 Sep | 172-4 v Brigg TownBrigg Town 4-2 Winterton Rangers | Northern Counties East League Division One |
| 11 | Wed 30 Sep | 32-0 v Kinsley BoysWinterton Rangers 2-0 Kinsley Boys | Northern Counties East League Division One |
| 12 | Sat 3 Oct | 32-1 v Selby TownSelby Town 1-2 Winterton Rangers | Northern Counties East League Division One |
| 13 | Sat 10 Oct | 32-3 v Route One RoversWinterton Rangers 2-3 Route One Rovers | Northern Counties East League Division One |
| 14 | Wed 14 Oct | 171-5 v Appleby FrodinghamWinterton Rangers 1-5 Appleby Frodingham | Lincolnshire Senior Trophy First Round |
| 15 | Sat 17 Oct | 35-0 v Athersley RecreationAthersley Recreation 0-5 Winterton Rangers | Northern Counties East League Division One |
| 16 | Sat 24 Oct | 32-3 v Crowle ColtsWinterton Rangers 2-3 Crowle Colts | Northern Counties East League Division One |
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