| 1 | Tue 18 Jul | 72-0 v Bottesford TownBottesford Town 0-2 Winterton Rangers | Friendly |
| 2 | Sat 22 Jul | 71-2 v Louth UnitedWinterton Rangers 1-2 Louth United | Friendly |
| 3 | Sat 5 Aug | 72-4 v Melton TownWinterton Rangers 2-4 Melton Town | Emirates FA Cup Extra Preliminary Round |
| 4 | Sat 12 Aug | 71-2 v Consett AFCWinterton Rangers 1-2 Consett AFC | Northern Premier League - East Division |
| 5 | Tue 15 Aug | 51-3 v Belper TownBelper Town 3-1 Winterton Rangers | Northern Premier League - East Division |
| 6 | Wed 23 Aug | 51-2 v Carlton TownWinterton Rangers 1-2 Carlton Town | Northern Premier League - East Division |
| 7 | Sat 26 Aug | 51-4 v Hebburn TownHebburn Town 4-1 Winterton Rangers | Northern Premier League - East Division |
| 8 | Mon 28 Aug | 51-0 v Bridlington TownWinterton Rangers 1-0 Bridlington Town | Northern Premier League - East Division |
| 9 | Sat 9 Sep | 51-2 v AvroAvro 2-1 Winterton Rangers | Isuzu FA Trophy First Qualifying Round |
| 10 | Sat 16 Sep | 7 0-3 v North FerribyNorth Ferriby 3-0 Winterton Rangers | Northern Premier League - East Division |
| 11 | Wed 27 Sep | 5 0-4 v Cleethorpes TownCleethorpes Town 4-0 Winterton Rangers | Northern Premier League - East Division |
| 12 | Sat 30 Sep | 52-1 v Stocksbridge Park SteelsWinterton Rangers 2-1 Stocksbridge Park Steels | Northern Premier League - East Division |
| 13 | Sat 21 Oct | 42-1 v Grimsby BoroughGrimsby Borough 1-2 Winterton Rangers | Northern Premier League - East Division |
| 14 | Sat 18 Nov | 142-1 v Grantham TownGrantham Town 1-2 Winterton Rangers | Northern Premier League - East Division |
| 15 | Sat 25 Nov | 60-3 v DunstonWinterton Rangers 0-3 Dunston | Northern Premier League - East Division |
| 16 | Sat 9 Dec | 11 2-4 v Ossett UnitedOssett United 4-2 Winterton Rangers | Northern Premier League - East Division |
| 17 | Sat 16 Dec | 80-2 v Belper TownWinterton Rangers 0-2 Belper Town | Northern Premier League - East Division |
| 18 | Sat 23 Dec | 11 0-0 v Consett AFCConsett AFC 0-0 Winterton Rangers | Northern Premier League - East Division |
| 19 | Tue 26 Dec | 21-2 v Brighouse TownWinterton Rangers 1-2 Brighouse Town | Northern Premier League - East Division |
| 20 | Sat 30 Dec | 110-2 v Bridlington TownBridlington Town 2-0 Winterton Rangers | Northern Premier League - East Division |
| 21 | Sat 6 Jan | 42-2 v Hebburn TownWinterton Rangers 2-2 Hebburn Town | Northern Premier League - East Division |
| 22 | Sat 13 Jan | 41-2 v Carlton TownCarlton Town 2-1 Winterton Rangers | Northern Premier League - East Division |
| 23 | Sat 27 Jan | 42-1 v Grimsby BoroughWinterton Rangers 2-1 Grimsby Borough | Northern Premier League - East Division |
| 24 | Sat 3 Feb | 42-3 v North FerribyWinterton Rangers 2-3 North Ferriby | Northern Premier League - East Division |
| 25 | Sat 10 Feb | 51-2 v Newton AycliffeWinterton Rangers 1-2 Newton Aycliffe | Northern Premier League - East Division |
| 26 | Sat 17 Feb | 41-2 v Stocksbridge Park SteelsStocksbridge Park Steels 2-1 Winterton Rangers | Northern Premier League - East Division |
| 27 | Sat 24 Feb | 70-0 v LiversedgeWinterton Rangers 0-0 Liversedge | Northern Premier League - East Division |
| 28 | Sat 16 Mar | 70-0 v Ossett UnitedWinterton Rangers 0-0 Ossett United | Northern Premier League - East Division |
| 29 | Tue 19 Mar | 40-4 v SheffieldSheffield 4-0 Winterton Rangers | Northern Premier League - East Division |
| 30 | Sat 23 Mar | 40-2 v Newton AycliffeNewton Aycliffe 2-0 Winterton Rangers | Northern Premier League - East Division |
| 31 | Sat 30 Mar | 40-2 v Cleethorpes TownWinterton Rangers 0-2 Cleethorpes Town | Northern Premier League - East Division |
| 32 | Mon 1 Apr | 55-1 v Brighouse TownBrighouse Town 1-5 Winterton Rangers | Northern Premier League - East Division |
| 33 | Sat 6 Apr | 20-3 v Pontefract CollieriesPontefract Collieries 3-0 Winterton Rangers | Northern Premier League - East Division |
| 34 | Sat 13 Apr | 11 1-0 v Stockton TownWinterton Rangers 1-0 Stockton Town | Northern Premier League - East Division |
| 35 | Tue 16 Apr | 40-0 v Ashington AFCAshington AFC 0-0 Winterton Rangers | Northern Premier League - East Division |
| 36 | Sat 20 Apr | 72-1 v DunstonDunston 1-2 Winterton Rangers | Northern Premier League - East Division |
| 37 | Sat 27 Apr | 92-0 v Grantham TownWinterton Rangers 2-0 Grantham Town | Northern Premier League - East Division |
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