| 1 | Tue 18 Jul | 142-0 v Bottesford TownBottesford Town 0-2 Winterton Rangers | Friendly |
| 2 | Sat 22 Jul | 91-2 v Louth UnitedWinterton Rangers 1-2 Louth United | Friendly |
| 3 | Sat 12 Aug | 141-2 v Consett AFCWinterton Rangers 1-2 Consett AFC | Northern Premier League - East Division |
| 4 | Tue 15 Aug | 141-3 v Belper TownBelper Town 3-1 Winterton Rangers | Northern Premier League - East Division |
| 5 | Wed 23 Aug | 141-2 v Carlton TownWinterton Rangers 1-2 Carlton Town | Northern Premier League - East Division |
| 6 | Sat 26 Aug | 101-4 v Hebburn TownHebburn Town 4-1 Winterton Rangers | Northern Premier League - East Division |
| 7 | Mon 28 Aug | 91-0 v Bridlington TownWinterton Rangers 1-0 Bridlington Town | Northern Premier League - East Division |
| 8 | Sat 9 Sep | 91-2 v AvroAvro 2-1 Winterton Rangers | Isuzu FA Trophy First Qualifying Round |
| 9 | Sat 16 Sep | 170-3 v North FerribyNorth Ferriby 3-0 Winterton Rangers | Northern Premier League - East Division |
| 10 | Wed 27 Sep | 110-4 v Cleethorpes TownCleethorpes Town 4-0 Winterton Rangers | Northern Premier League - East Division |
| 11 | Sat 30 Sep | 92-1 v Stocksbridge Park SteelsWinterton Rangers 2-1 Stocksbridge Park Steels | Northern Premier League - East Division |
| 12 | Wed 4 Oct | 71-2 v Cleethorpes TownCleethorpes Town 2-1 Winterton Rangers | Lincolnshire Senior Cup Quarter Final |
| 13 | Sat 7 Oct | 91-5 v LiversedgeLiversedge 5-1 Winterton Rangers | Northern Premier League - East Division |
| 14 | Sat 14 Oct | 140-4 v Ashington AFCWinterton Rangers 0-4 Ashington AFC | Northern Premier League - East Division |
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