| 1 | Tue 18 Jul | 122-0 v Bottesford TownBottesford Town 0-2 Winterton Rangers | Friendly |
| 2 | Sat 22 Jul | 21-2 v Louth UnitedWinterton Rangers 1-2 Louth United | Friendly |
| 3 | Sat 5 Aug | 2 2-4 v Melton TownWinterton Rangers 2-4 Melton Town | Emirates FA Cup Extra Preliminary Round |
| 4 | Sat 12 Aug | 21-2 v Consett AFCWinterton Rangers 1-2 Consett AFC | Northern Premier League - East Division |
| 5 | Tue 15 Aug | 2 1-3 v Belper TownBelper Town 3-1 Winterton Rangers | Northern Premier League - East Division |
| 6 | Wed 23 Aug | 21-2 v Carlton TownWinterton Rangers 1-2 Carlton Town | Northern Premier League - East Division |
| 7 | Sat 26 Aug | 21-4 v Hebburn TownHebburn Town 4-1 Winterton Rangers | Northern Premier League - East Division |
| 8 | Mon 28 Aug | 21-0 v Bridlington TownWinterton Rangers 1-0 Bridlington Town | Northern Premier League - East Division |
| 9 | Sat 9 Sep | 21-2 v AvroAvro 2-1 Winterton Rangers | Isuzu FA Trophy First Qualifying Round |
| 10 | Sat 16 Sep | 20-3 v North FerribyNorth Ferriby 3-0 Winterton Rangers | Northern Premier League - East Division |
| 11 | Wed 27 Sep | 20-4 v Cleethorpes TownCleethorpes Town 4-0 Winterton Rangers | Northern Premier League - East Division |
| 12 | Sat 30 Sep | 22-1 v Stocksbridge Park SteelsWinterton Rangers 2-1 Stocksbridge Park Steels | Northern Premier League - East Division |
| 13 | Wed 4 Oct | 21-2 v Cleethorpes TownCleethorpes Town 2-1 Winterton Rangers | Lincolnshire Senior Cup Quarter Final |
| 14 | Sat 7 Oct | 21-5 v LiversedgeLiversedge 5-1 Winterton Rangers | Northern Premier League - East Division |
| 15 | Sat 14 Oct | 20-4 v Ashington AFCWinterton Rangers 0-4 Ashington AFC | Northern Premier League - East Division |
| 16 | Sat 21 Oct | 22-1 v Grimsby BoroughGrimsby Borough 1-2 Winterton Rangers | Northern Premier League - East Division |
| 17 | Sat 28 Oct | 22-0 v SheffieldWinterton Rangers 2-0 Sheffield | Northern Premier League - East Division |
| 18 | Sat 4 Nov | 20-2 v Stockton TownStockton Town 2-0 Winterton Rangers | Northern Premier League - East Division |
| 19 | Sat 11 Nov | 2 1-4 v Pontefract CollieriesWinterton Rangers 1-4 Pontefract Collieries | Northern Premier League - East Division |
| 20 | Sat 18 Nov | 22-1 v Grantham TownGrantham Town 1-2 Winterton Rangers | Northern Premier League - East Division |
| 21 | Sat 25 Nov | 20-3 v DunstonWinterton Rangers 0-3 Dunston | Northern Premier League - East Division |
| 22 | Sat 9 Dec | 22-4 v Ossett UnitedOssett United 4-2 Winterton Rangers | Northern Premier League - East Division |
| 23 | Sat 16 Dec | 110-2 v Belper TownWinterton Rangers 0-2 Belper Town | Northern Premier League - East Division |
| 24 | Sat 23 Dec | 20-0 v Consett AFCConsett AFC 0-0 Winterton Rangers | Northern Premier League - East Division |
| 25 | Sat 27 Jan | 22-1 v Grimsby BoroughWinterton Rangers 2-1 Grimsby Borough | Northern Premier League - East Division |
| 26 | Sat 3 Feb | 22-3 v North FerribyWinterton Rangers 2-3 North Ferriby | Northern Premier League - East Division |
| 27 | Sat 10 Feb | 21-2 v Newton AycliffeWinterton Rangers 1-2 Newton Aycliffe | Northern Premier League - East Division |
| 28 | Sat 17 Feb | 21-2 v Stocksbridge Park SteelsStocksbridge Park Steels 2-1 Winterton Rangers | Northern Premier League - East Division |
| 29 | Sat 24 Feb | 20-0 v LiversedgeWinterton Rangers 0-0 Liversedge | Northern Premier League - East Division |
| 30 | Sat 16 Mar | 20-0 v Ossett UnitedWinterton Rangers 0-0 Ossett United | Northern Premier League - East Division |
| 31 | Tue 19 Mar | 20-4 v SheffieldSheffield 4-0 Winterton Rangers | Northern Premier League - East Division |
| 32 | Sat 23 Mar | 20-2 v Newton AycliffeNewton Aycliffe 2-0 Winterton Rangers | Northern Premier League - East Division |
| 33 | Sat 30 Mar | 20-2 v Cleethorpes TownWinterton Rangers 0-2 Cleethorpes Town | Northern Premier League - East Division |
| 34 | Mon 1 Apr | 25-1 v Brighouse TownBrighouse Town 1-5 Winterton Rangers | Northern Premier League - East Division |
| 35 | Sat 13 Apr | 21-0 v Stockton TownWinterton Rangers 1-0 Stockton Town | Northern Premier League - East Division |
| 36 | Tue 16 Apr | 20-0 v Ashington AFCAshington AFC 0-0 Winterton Rangers | Northern Premier League - East Division |
| 37 | Sat 20 Apr | 22-1 v DunstonDunston 1-2 Winterton Rangers | Northern Premier League - East Division |
| 38 | Sat 27 Apr | 22-0 v Grantham TownWinterton Rangers 2-0 Grantham Town | Northern Premier League - East Division |
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