| 1 | Tue 18 Jul | 32-0 v Bottesford TownBottesford Town 0-2 Winterton Rangers | Friendly |
| 2 | Sat 22 Jul | 41-2 v Louth UnitedWinterton Rangers 1-2 Louth United | Friendly |
| 3 | Tue 15 Aug | 171-3 v Belper TownBelper Town 3-1 Winterton Rangers | Northern Premier League - East Division |
| 4 | Wed 23 Aug | 4 1-2 v Carlton TownWinterton Rangers 1-2 Carlton Town | Northern Premier League - East Division |
| 5 | Sat 26 Aug | 4 1-4 v Hebburn TownHebburn Town 4-1 Winterton Rangers | Northern Premier League - East Division |
| 6 | Mon 28 Aug | 41-0 v Bridlington TownWinterton Rangers 1-0 Bridlington Town | Northern Premier League - East Division |
| 7 | Sat 9 Sep | 3 1-2 v AvroAvro 2-1 Winterton Rangers | Isuzu FA Trophy First Qualifying Round |
| 8 | Sat 16 Sep | 4 0-3 v North FerribyNorth Ferriby 3-0 Winterton Rangers | Northern Premier League - East Division |
| 9 | Sat 30 Sep | 42-1 v Stocksbridge Park SteelsWinterton Rangers 2-1 Stocksbridge Park Steels | Northern Premier League - East Division |
| 10 | Wed 4 Oct | 41-2 v Cleethorpes TownCleethorpes Town 2-1 Winterton Rangers | Lincolnshire Senior Cup Quarter Final |
| 11 | Sat 7 Oct | 151-5 v LiversedgeLiversedge 5-1 Winterton Rangers | Northern Premier League - East Division |
| 12 | Sat 14 Oct | 4 0-4 v Ashington AFCWinterton Rangers 0-4 Ashington AFC | Northern Premier League - East Division |
| 13 | Sat 21 Oct | 8 2-1 v Grimsby BoroughGrimsby Borough 1-2 Winterton Rangers | Northern Premier League - East Division |
| 14 | Sat 28 Oct | 4 2-0 v SheffieldWinterton Rangers 2-0 Sheffield | Northern Premier League - East Division |
| 15 | Sat 11 Nov | 81-4 v Pontefract CollieriesWinterton Rangers 1-4 Pontefract Collieries | Northern Premier League - East Division |
| 16 | Sat 18 Nov | 82-1 v Grantham TownGrantham Town 1-2 Winterton Rangers | Northern Premier League - East Division |
| 17 | Sat 25 Nov | 80-3 v DunstonWinterton Rangers 0-3 Dunston | Northern Premier League - East Division |
| 18 | Sat 9 Dec | 82-4 v Ossett UnitedOssett United 4-2 Winterton Rangers | Northern Premier League - East Division |
| 19 | Sat 16 Dec | 40-2 v Belper TownWinterton Rangers 0-2 Belper Town | Northern Premier League - East Division |
| 20 | Sat 23 Dec | 80-0 v Consett AFCConsett AFC 0-0 Winterton Rangers | Northern Premier League - East Division |
| 21 | Tue 26 Dec | 8 1-2 v Brighouse TownWinterton Rangers 1-2 Brighouse Town | Northern Premier League - East Division |
| 22 | Sat 30 Dec | 40-2 v Bridlington TownBridlington Town 2-0 Winterton Rangers | Northern Premier League - East Division |
| 23 | Sat 6 Jan | 82-2 v Hebburn TownWinterton Rangers 2-2 Hebburn Town | Northern Premier League - East Division |
| 24 | Sat 27 Jan | 82-1 v Grimsby BoroughWinterton Rangers 2-1 Grimsby Borough | Northern Premier League - East Division |
| 25 | Sat 3 Feb | 82-3 v North FerribyWinterton Rangers 2-3 North Ferriby | Northern Premier League - East Division |
| 26 | Sat 10 Feb | 4 1-2 v Newton AycliffeWinterton Rangers 1-2 Newton Aycliffe | Northern Premier League - East Division |
| 27 | Sat 27 Apr | 162-0 v Grantham TownWinterton Rangers 2-0 Grantham Town | Northern Premier League - East Division |
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