| 1 | Sat 22 Jul | 31-2 v Louth UnitedWinterton Rangers 1-2 Louth United | Friendly |
| 2 | Sat 5 Aug | 32-4 v Melton TownWinterton Rangers 2-4 Melton Town | Emirates FA Cup Extra Preliminary Round |
| 3 | Sat 12 Aug | 31-2 v Consett AFCWinterton Rangers 1-2 Consett AFC | Northern Premier League - East Division |
| 4 | Tue 15 Aug | 31-3 v Belper TownBelper Town 3-1 Winterton Rangers | Northern Premier League - East Division |
| 5 | Wed 23 Aug | 31-2 v Carlton TownWinterton Rangers 1-2 Carlton Town | Northern Premier League - East Division |
| 6 | Sat 26 Aug | 3 1-4 v Hebburn TownHebburn Town 4-1 Winterton Rangers | Northern Premier League - East Division |
| 7 | Mon 28 Aug | 31-0 v Bridlington TownWinterton Rangers 1-0 Bridlington Town | Northern Premier League - East Division |
| 8 | Sat 16 Sep | 3 0-3 v North FerribyNorth Ferriby 3-0 Winterton Rangers | Northern Premier League - East Division |
| 9 | Sat 30 Sep | 72-1 v Stocksbridge Park SteelsWinterton Rangers 2-1 Stocksbridge Park Steels | Northern Premier League - East Division |
| 10 | Sat 7 Oct | 71-5 v LiversedgeLiversedge 5-1 Winterton Rangers | Northern Premier League - East Division |
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