| 1 | Tue 18 Jul | 112-0 v Bottesford TownBottesford Town 0-2 Winterton Rangers | Friendly |
| 2 | Sat 22 Jul | 111-2 v Louth UnitedWinterton Rangers 1-2 Louth United | Friendly |
| 3 | Sat 5 Aug | 112-4 v Melton TownWinterton Rangers 2-4 Melton Town | Emirates FA Cup Extra Preliminary Round |
| 4 | Sat 12 Aug | 41-2 v Consett AFCWinterton Rangers 1-2 Consett AFC | Northern Premier League - East Division |
| 5 | Tue 15 Aug | 71-3 v Belper TownBelper Town 3-1 Winterton Rangers | Northern Premier League - East Division |
| 6 | Wed 23 Aug | 7 1-2 v Carlton TownWinterton Rangers 1-2 Carlton Town | Northern Premier League - East Division |
| 7 | Sat 26 Aug | 71-4 v Hebburn TownHebburn Town 4-1 Winterton Rangers | Northern Premier League - East Division |
| 8 | Mon 28 Aug | 71-0 v Bridlington TownWinterton Rangers 1-0 Bridlington Town | Northern Premier League - East Division |
| 9 | Sat 9 Sep | 4 1-2 v AvroAvro 2-1 Winterton Rangers | Isuzu FA Trophy First Qualifying Round |
| 10 | Sat 16 Sep | 100-3 v North FerribyNorth Ferriby 3-0 Winterton Rangers | Northern Premier League - East Division |
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