| 1 | Wed 26 Aug | 12-1 v South LeedsWinterton Rangers 2-1 South Leeds | Northern Counties East League Division One |
| 2 | Sat 5 Sep | 12-1 v Leeds UFCAWinterton Rangers 2-1 Leeds UFCA | Northern Counties East League Division One |
| 3 | Sat 12 Sep | 13-1 v Armthorpe WelfareWinterton Rangers 3-1 Armthorpe Welfare | Northern Counties East League Division One |
| 4 | Tue 15 Sep | 10-3 v Goole AFCGoole AFC 3-0 Winterton Rangers | Northern Counties East League Division One |
| 5 | Sat 19 Sep | 12-2 v Ilkley TownWinterton Rangers 2-2 Ilkley Town | Northern Counties East League Division One |
| 6 | Sat 26 Sep | 12-4 v Brigg TownBrigg Town 4-2 Winterton Rangers | Northern Counties East League Division One |
| 7 | Wed 30 Sep | 12-0 v Kinsley BoysWinterton Rangers 2-0 Kinsley Boys | Northern Counties East League Division One |
| 8 | Sat 3 Oct | 1 2-1 v Selby TownSelby Town 1-2 Winterton Rangers | Northern Counties East League Division One |
| 9 | Sat 10 Oct | 12-3 v Route One RoversWinterton Rangers 2-3 Route One Rovers | Northern Counties East League Division One |
| 10 | Wed 14 Oct | 11-5 v Appleby FrodinghamWinterton Rangers 1-5 Appleby Frodingham | Lincolnshire Senior Trophy First Round |
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