| 1 | Sat 26 Jul | 41-0 v Nostell Miners WelfareNostell Miners Welfare 0-1 Winterton Rangers | Northern Counties East League Division One |
| 2 | Sat 2 Aug | 43-4 v Athersley RecreationWinterton Rangers 3-4 Athersley Recreation | Northern Counties East League Division One |
| 3 | Wed 6 Aug | 42-3 v Armthorpe WelfareWinterton Rangers 2-3 Armthorpe Welfare | Northern Counties East League Division One |
| 4 | Sat 9 Aug | 20-1 v Club Thorne CollieryClub Thorne Colliery 1-0 Winterton Rangers | Northern Counties East League Division One |
| 5 | Sat 23 Aug | 20-2 v Northwich VictoriaNorthwich Victoria 2-0 Winterton Rangers | Isuzu FA Vase First Qualifying Round |
| 6 | Wed 27 Aug | 60-2 v Doncaster CityDoncaster City 2-0 Winterton Rangers | Northern Counties East League Division One |
| 7 | Sat 30 Aug | 41-4 v Goole AFCWinterton Rangers 1-4 Goole AFC | Northern Counties East League Division One |
| 8 | Wed 3 Sep | 40-1 v WakefieldWinterton Rangers 0-1 Wakefield | Northern Counties East League Division One |
| 9 | Sat 6 Sep | 41-4 v Crowle ColtsCrowle Colts 4-1 Winterton Rangers | Northern Counties East League Division One |
| 10 | Sat 13 Sep | 40-1 v Selby TownWinterton Rangers 0-1 Selby Town | Northern Counties East League Division One |
| 11 | Sat 8 Nov | 40-2 v Louth TownLouth Town 2-0 Winterton Rangers | Northern Counties East League Division One |
| 12 | Sat 22 Nov | 23-0 v Nostell Miners WelfareWinterton Rangers 3-0 Nostell Miners Welfare | Northern Counties East League Division One |
| 13 | Wed 26 Nov | 51-6 v Route One RoversWinterton Rangers 1-6 Route One Rovers | Northern Counties East League Cup Third Round |
| 14 | Sat 13 Dec | 122-4 v Club Thorne CollieryWinterton Rangers 2-4 Club Thorne Colliery | Northern Counties East League Division One |
| 15 | Sat 3 Jan | 23-1 v Goole AFCGoole AFC 1-3 Winterton Rangers | Northern Counties East League Division One |
| 16 | Tue 13 Jan | 21-1 v Armthorpe WelfareArmthorpe Welfare 1-1 Winterton Rangers | Northern Counties East League Division One |
| 17 | Sat 17 Jan | 20-3 v Selby TownSelby Town 3-0 Winterton Rangers | Northern Counties East League Division One |
| 18 | Sat 24 Jan | 21-2 v Worsbrough Bridge AthleticWinterton Rangers 1-2 Worsbrough Bridge Athletic | Northern Counties East League Division One |
| 19 | Fri 30 Jan | 20-3 v WakefieldWakefield 3-0 Winterton Rangers | Northern Counties East League Division One |
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