| 1 | Tue 18 Jul | 12-0 v Bottesford TownBottesford Town 0-2 Winterton Rangers | Friendly |
| 2 | Sat 5 Aug | 12-4 v Melton TownWinterton Rangers 2-4 Melton Town | Emirates FA Cup Extra Preliminary Round |
| 3 | Sat 12 Aug | 11-2 v Consett AFCWinterton Rangers 1-2 Consett AFC | Northern Premier League - East Division |
| 4 | Tue 15 Aug | 11-3 v Belper TownBelper Town 3-1 Winterton Rangers | Northern Premier League - East Division |
| 5 | Wed 23 Aug | 1 1-2 v Carlton TownWinterton Rangers 1-2 Carlton Town | Northern Premier League - East Division |
| 6 | Sat 26 Aug | 11-4 v Hebburn TownHebburn Town 4-1 Winterton Rangers | Northern Premier League - East Division |
| 7 | Mon 28 Aug | 11-0 v Bridlington TownWinterton Rangers 1-0 Bridlington Town | Northern Premier League - East Division |
| 8 | Sat 9 Sep | 11-2 v AvroAvro 2-1 Winterton Rangers | Isuzu FA Trophy First Qualifying Round |
| 9 | Sat 16 Sep | 10-3 v North FerribyNorth Ferriby 3-0 Winterton Rangers | Northern Premier League - East Division |
| 10 | Wed 27 Sep | 10-4 v Cleethorpes TownCleethorpes Town 4-0 Winterton Rangers | Northern Premier League - East Division |
| 11 | Sat 30 Sep | 12-1 v Stocksbridge Park SteelsWinterton Rangers 2-1 Stocksbridge Park Steels | Northern Premier League - East Division |
| 12 | Wed 4 Oct | 11-2 v Cleethorpes TownCleethorpes Town 2-1 Winterton Rangers | Lincolnshire Senior Cup Quarter Final |
| 13 | Sat 7 Oct | 11-5 v LiversedgeLiversedge 5-1 Winterton Rangers | Northern Premier League - East Division |
| 14 | Sat 14 Oct | 10-4 v Ashington AFCWinterton Rangers 0-4 Ashington AFC | Northern Premier League - East Division |
| 15 | Sat 21 Oct | 12-1 v Grimsby BoroughGrimsby Borough 1-2 Winterton Rangers | Northern Premier League - East Division |
| 16 | Sat 28 Oct | 12-0 v SheffieldWinterton Rangers 2-0 Sheffield | Northern Premier League - East Division |
| 17 | Sat 4 Nov | 10-2 v Stockton TownStockton Town 2-0 Winterton Rangers | Northern Premier League - East Division |
| 18 | Sat 11 Nov | 11-4 v Pontefract CollieriesWinterton Rangers 1-4 Pontefract Collieries | Northern Premier League - East Division |
| 19 | Sat 18 Nov | 12-1 v Grantham TownGrantham Town 1-2 Winterton Rangers | Northern Premier League - East Division |
| 20 | Sat 25 Nov | 1 0-3 v DunstonWinterton Rangers 0-3 Dunston | Northern Premier League - East Division |
| 21 | Sat 16 Dec | 10-2 v Belper TownWinterton Rangers 0-2 Belper Town | Northern Premier League - East Division |
| 22 | Sat 23 Dec | 10-0 v Consett AFCConsett AFC 0-0 Winterton Rangers | Northern Premier League - East Division |
| 23 | Sat 30 Dec | 10-2 v Bridlington TownBridlington Town 2-0 Winterton Rangers | Northern Premier League - East Division |
| 24 | Sat 6 Jan | 12-2 v Hebburn TownWinterton Rangers 2-2 Hebburn Town | Northern Premier League - East Division |
| 25 | Sat 13 Jan | 11-2 v Carlton TownCarlton Town 2-1 Winterton Rangers | Northern Premier League - East Division |
| 26 | Sat 27 Jan | 12-1 v Grimsby BoroughWinterton Rangers 2-1 Grimsby Borough | Northern Premier League - East Division |
| 27 | Sat 3 Feb | 12-3 v North FerribyWinterton Rangers 2-3 North Ferriby | Northern Premier League - East Division |
| 28 | Sat 10 Feb | 11-2 v Newton AycliffeWinterton Rangers 1-2 Newton Aycliffe | Northern Premier League - East Division |
| 29 | Sat 17 Feb | 11-2 v Stocksbridge Park SteelsStocksbridge Park Steels 2-1 Winterton Rangers | Northern Premier League - East Division |
| 30 | Sat 24 Feb | 10-0 v LiversedgeWinterton Rangers 0-0 Liversedge | Northern Premier League - East Division |
| 31 | Sat 16 Mar | 10-0 v Ossett UnitedWinterton Rangers 0-0 Ossett United | Northern Premier League - East Division |
| 32 | Tue 19 Mar | 10-4 v SheffieldSheffield 4-0 Winterton Rangers | Northern Premier League - East Division |
| 33 | Sat 23 Mar | 10-2 v Newton AycliffeNewton Aycliffe 2-0 Winterton Rangers | Northern Premier League - East Division |
| 34 | Sat 30 Mar | 10-2 v Cleethorpes TownWinterton Rangers 0-2 Cleethorpes Town | Northern Premier League - East Division |
| 35 | Mon 1 Apr | 15-1 v Brighouse TownBrighouse Town 1-5 Winterton Rangers | Northern Premier League - East Division |
| 36 | Sat 6 Apr | 10-3 v Pontefract CollieriesPontefract Collieries 3-0 Winterton Rangers | Northern Premier League - East Division |
| 37 | Sat 13 Apr | 11-0 v Stockton TownWinterton Rangers 1-0 Stockton Town | Northern Premier League - East Division |
| 38 | Tue 16 Apr | 10-0 v Ashington AFCAshington AFC 0-0 Winterton Rangers | Northern Premier League - East Division |
| 39 | Sat 20 Apr | 12-1 v DunstonDunston 1-2 Winterton Rangers | Northern Premier League - East Division |
| 40 | Sat 27 Apr | 12-0 v Grantham TownWinterton Rangers 2-0 Grantham Town | Northern Premier League - East Division |
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