| 1 | Wed 30 Jul | 14-2 v Club Thorne CollieryWinterton Rangers 4-2 Club Thorne Colliery | Northern Counties East League Cup First Round |
| 2 | Sat 2 Aug | 13-4 v Athersley RecreationWinterton Rangers 3-4 Athersley Recreation | Northern Counties East League Division One |
| 3 | Wed 6 Aug | 12-3 v Armthorpe WelfareWinterton Rangers 2-3 Armthorpe Welfare | Northern Counties East League Division One |
| 4 | Sat 9 Aug | 10-1 v Club Thorne CollieryClub Thorne Colliery 1-0 Winterton Rangers | Northern Counties East League Division One |
| 5 | Sat 16 Aug | 11-3 v Brigg TownBrigg Town 3-1 Winterton Rangers | Northern Counties East League Division One |
| 6 | Sat 30 Aug | 11-4 v Goole AFCWinterton Rangers 1-4 Goole AFC | Northern Counties East League Division One |
| 7 | Wed 3 Sep | 1 0-1 v WakefieldWinterton Rangers 0-1 Wakefield | Northern Counties East League Division One |
| 8 | Sat 11 Oct | 11-5 v Grantham TownGrantham Town 5-1 Winterton Rangers | Lincolnshire Senior Trophy First Round |
| 9 | Wed 15 Oct | 11-9 v Route One RoversRoute One Rovers 9-1 Winterton Rangers | Northern Counties East League Division One |
| 10 | Sat 18 Oct | 12-1 v Glasshoughton WelfareWinterton Rangers 2-1 Glasshoughton Welfare | Northern Counties East League Division One |
| 11 | Wed 22 Oct | 11-1 v Ilkley TownWinterton Rangers 1-1 Ilkley Town | Northern Counties East League Division One |
| 12 | Sat 25 Oct | 11-4 v Harrogate Railway AthleticHarrogate Railway Athletic 4-1 Winterton Rangers | Northern Counties East League Division One |
| 13 | Sat 8 Nov | 10-2 v Louth TownLouth Town 2-0 Winterton Rangers | Northern Counties East League Division One |
| 14 | Sat 15 Nov | 11-3 v South LeedsWinterton Rangers 1-3 South Leeds | Northern Counties East League Division One |
| 15 | Sat 22 Nov | 13-0 v Nostell Miners WelfareWinterton Rangers 3-0 Nostell Miners Welfare | Northern Counties East League Division One |
| 16 | Sat 6 Dec | 13-0 v Athersley RecreationAthersley Recreation 0-3 Winterton Rangers | Northern Counties East League Division One |
| 17 | Sat 13 Dec | 12-4 v Club Thorne CollieryWinterton Rangers 2-4 Club Thorne Colliery | Northern Counties East League Division One |
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