| 1 | Sat 6 Dec | 9 3-0 v Athersley RecreationAthersley Recreation 0-3 Winterton Rangers | Northern Counties East League Division One |
| 2 | Sat 13 Dec | 92-4 v Club Thorne CollieryWinterton Rangers 2-4 Club Thorne Colliery | Northern Counties East League Division One |
| 3 | Sat 3 Jan | 163-1 v Goole AFCGoole AFC 1-3 Winterton Rangers | Northern Counties East League Division One |
| 4 | Tue 13 Jan | 161-1 v Armthorpe WelfareArmthorpe Welfare 1-1 Winterton Rangers | Northern Counties East League Division One |
| 5 | Sat 17 Jan | 180-3 v Selby TownSelby Town 3-0 Winterton Rangers | Northern Counties East League Division One |
| 6 | Sat 24 Jan | 18 1-2 v Worsbrough Bridge AthleticWinterton Rangers 1-2 Worsbrough Bridge Athletic | Northern Counties East League Division One |
| 7 | Fri 30 Jan | 160-3 v WakefieldWakefield 3-0 Winterton Rangers | Northern Counties East League Division One |
| 8 | Wed 4 Feb | 16 0-1 v Brigg TownWinterton Rangers 0-1 Brigg Town | Northern Counties East League Division One |
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