| 1 | Tue 18 Jul | 62-0 v Bottesford TownBottesford Town 0-2 Winterton Rangers | Friendly |
| 2 | Sat 22 Jul | 61-2 v Louth UnitedWinterton Rangers 1-2 Louth United | Friendly |
| 3 | Sat 5 Aug | 6 2-4 v Melton TownWinterton Rangers 2-4 Melton Town | Emirates FA Cup Extra Preliminary Round |
| 4 | Sat 12 Aug | 6 1-2 v Consett AFCWinterton Rangers 1-2 Consett AFC | Northern Premier League - East Division |
| 5 | Tue 15 Aug | 61-3 v Belper TownBelper Town 3-1 Winterton Rangers | Northern Premier League - East Division |
| 6 | Sat 9 Sep | 6 1-2 v AvroAvro 2-1 Winterton Rangers | Isuzu FA Trophy First Qualifying Round |
| 7 | Sat 16 Sep | 6 0-3 v North FerribyNorth Ferriby 3-0 Winterton Rangers | Northern Premier League - East Division |
| 8 | Wed 27 Sep | 6 0-4 v Cleethorpes TownCleethorpes Town 4-0 Winterton Rangers | Northern Premier League - East Division |
| 9 | Sat 30 Sep | 62-1 v Stocksbridge Park SteelsWinterton Rangers 2-1 Stocksbridge Park Steels | Northern Premier League - East Division |
| 10 | Wed 4 Oct | 61-2 v Cleethorpes TownCleethorpes Town 2-1 Winterton Rangers | Lincolnshire Senior Cup Quarter Final |
| 11 | Sat 14 Oct | 6 0-4 v Ashington AFCWinterton Rangers 0-4 Ashington AFC | Northern Premier League - East Division |
| 12 | Sat 4 Nov | 150-2 v Stockton TownStockton Town 2-0 Winterton Rangers | Northern Premier League - East Division |
| 13 | Sat 11 Nov | 61-4 v Pontefract CollieriesWinterton Rangers 1-4 Pontefract Collieries | Northern Premier League - East Division |
| 14 | Sat 18 Nov | 6 2-1 v Grantham TownGrantham Town 1-2 Winterton Rangers | Northern Premier League - East Division |
| 15 | Sat 9 Dec | 6 2-4 v Ossett UnitedOssett United 4-2 Winterton Rangers | Northern Premier League - East Division |
| 16 | Sat 16 Dec | 6 0-2 v Belper TownWinterton Rangers 0-2 Belper Town | Northern Premier League - East Division |
| 17 | Sat 23 Dec | 60-0 v Consett AFCConsett AFC 0-0 Winterton Rangers | Northern Premier League - East Division |
| 18 | Tue 26 Dec | 61-2 v Brighouse TownWinterton Rangers 1-2 Brighouse Town | Northern Premier League - East Division |
| 19 | Sat 30 Dec | 60-2 v Bridlington TownBridlington Town 2-0 Winterton Rangers | Northern Premier League - East Division |
| 20 | Sat 6 Jan | 62-2 v Hebburn TownWinterton Rangers 2-2 Hebburn Town | Northern Premier League - East Division |
| 21 | Sat 13 Jan | 6 1-2 v Carlton TownCarlton Town 2-1 Winterton Rangers | Northern Premier League - East Division |
| 22 | Sat 27 Jan | 62-1 v Grimsby BoroughWinterton Rangers 2-1 Grimsby Borough | Northern Premier League - East Division |
| 23 | Sat 3 Feb | 6 2-3 v North FerribyWinterton Rangers 2-3 North Ferriby | Northern Premier League - East Division |
| 24 | Sat 17 Feb | 61-2 v Stocksbridge Park SteelsStocksbridge Park Steels 2-1 Winterton Rangers | Northern Premier League - East Division |
| 25 | Sat 24 Feb | 60-0 v LiversedgeWinterton Rangers 0-0 Liversedge | Northern Premier League - East Division |
| 26 | Sat 16 Mar | 60-0 v Ossett UnitedWinterton Rangers 0-0 Ossett United | Northern Premier League - East Division |
| 27 | Tue 19 Mar | 6 0-4 v SheffieldSheffield 4-0 Winterton Rangers | Northern Premier League - East Division |
| 28 | Sat 23 Mar | 60-2 v Newton AycliffeNewton Aycliffe 2-0 Winterton Rangers | Northern Premier League - East Division |
| 29 | Sat 6 Apr | 60-3 v Pontefract CollieriesPontefract Collieries 3-0 Winterton Rangers | Northern Premier League - East Division |
| 30 | Sat 13 Apr | 6 1-0 v Stockton TownWinterton Rangers 1-0 Stockton Town | Northern Premier League - East Division |
| 31 | Tue 16 Apr | 60-0 v Ashington AFCAshington AFC 0-0 Winterton Rangers | Northern Premier League - East Division |
| 32 | Sat 20 Apr | 6 2-1 v DunstonDunston 1-2 Winterton Rangers | Northern Premier League - East Division |
| 33 | Sat 27 Apr | 62-0 v Grantham TownWinterton Rangers 2-0 Grantham Town | Northern Premier League - East Division |
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