| 1 | Tue 18 Jul | 52-0 v Bottesford TownBottesford Town 0-2 Winterton Rangers | Friendly |
| 2 | Sat 22 Jul | 51-2 v Louth UnitedWinterton Rangers 1-2 Louth United | Friendly |
| 3 | Sat 5 Aug | 52-4 v Melton TownWinterton Rangers 2-4 Melton Town | Emirates FA Cup Extra Preliminary Round |
| 4 | Sat 12 Aug | 51-2 v Consett AFCWinterton Rangers 1-2 Consett AFC | Northern Premier League - East Division |
| 5 | Sat 9 Sep | 161-2 v AvroAvro 2-1 Winterton Rangers | Isuzu FA Trophy First Qualifying Round |
| 6 | Wed 27 Sep | 40-4 v Cleethorpes TownCleethorpes Town 4-0 Winterton Rangers | Northern Premier League - East Division |
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