| 1 | Wed 27 Sep | 30-4 v Cleethorpes TownCleethorpes Town 4-0 Winterton Rangers | Northern Premier League - East Division |
| 2 | Sat 30 Sep | 3 2-1 v Stocksbridge Park SteelsWinterton Rangers 2-1 Stocksbridge Park Steels | Northern Premier League - East Division |
| 3 | Wed 4 Oct | 31-2 v Cleethorpes TownCleethorpes Town 2-1 Winterton Rangers | Lincolnshire Senior Cup Quarter Final |
| 4 | Sat 7 Oct | 31-5 v LiversedgeLiversedge 5-1 Winterton Rangers | Northern Premier League - East Division |
| 5 | Sat 14 Oct | 30-4 v Ashington AFCWinterton Rangers 0-4 Ashington AFC | Northern Premier League - East Division |
| 6 | Sat 21 Oct | 32-1 v Grimsby BoroughGrimsby Borough 1-2 Winterton Rangers | Northern Premier League - East Division |
| 7 | Sat 28 Oct | 32-0 v SheffieldWinterton Rangers 2-0 Sheffield | Northern Premier League - East Division |
| 8 | Sat 4 Nov | 30-2 v Stockton TownStockton Town 2-0 Winterton Rangers | Northern Premier League - East Division |
| 9 | Sat 11 Nov | 31-4 v Pontefract CollieriesWinterton Rangers 1-4 Pontefract Collieries | Northern Premier League - East Division |
| 10 | Sat 18 Nov | 32-1 v Grantham TownGrantham Town 1-2 Winterton Rangers | Northern Premier League - East Division |
| 11 | Sat 25 Nov | 30-3 v DunstonWinterton Rangers 0-3 Dunston | Northern Premier League - East Division |
| 12 | Sat 9 Dec | 32-4 v Ossett UnitedOssett United 4-2 Winterton Rangers | Northern Premier League - East Division |
| 13 | Sat 16 Dec | 30-2 v Belper TownWinterton Rangers 0-2 Belper Town | Northern Premier League - East Division |
| 14 | Sat 23 Dec | 30-0 v Consett AFCConsett AFC 0-0 Winterton Rangers | Northern Premier League - East Division |
| 15 | Tue 26 Dec | 31-2 v Brighouse TownWinterton Rangers 1-2 Brighouse Town | Northern Premier League - East Division |
| 16 | Sat 30 Dec | 3 0-2 v Bridlington TownBridlington Town 2-0 Winterton Rangers | Northern Premier League - East Division |
| 17 | Sat 6 Jan | 3 2-2 v Hebburn TownWinterton Rangers 2-2 Hebburn Town | Northern Premier League - East Division |
| 18 | Sat 13 Jan | 31-2 v Carlton TownCarlton Town 2-1 Winterton Rangers | Northern Premier League - East Division |
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