| 1 | Wed 27 Sep | 90-4 v Cleethorpes TownCleethorpes Town 4-0 Winterton Rangers | Northern Premier League - East Division |
| 2 | Sat 30 Sep | 162-1 v Stocksbridge Park SteelsWinterton Rangers 2-1 Stocksbridge Park Steels | Northern Premier League - East Division |
| 3 | Wed 4 Oct | 91-2 v Cleethorpes TownCleethorpes Town 2-1 Winterton Rangers | Lincolnshire Senior Cup Quarter Final |
| 4 | Sat 14 Oct | 90-4 v Ashington AFCWinterton Rangers 0-4 Ashington AFC | Northern Premier League - East Division |
| 5 | Sat 18 Nov | 162-1 v Grantham TownGrantham Town 1-2 Winterton Rangers | Northern Premier League - East Division |
| 6 | Sat 30 Dec | 150-2 v Bridlington TownBridlington Town 2-0 Winterton Rangers | Northern Premier League - East Division |
| 7 | Sat 6 Jan | 152-2 v Hebburn TownWinterton Rangers 2-2 Hebburn Town | Northern Premier League - East Division |
| 8 | Sat 13 Jan | 161-2 v Carlton TownCarlton Town 2-1 Winterton Rangers | Northern Premier League - East Division |
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