Against a side that included the likes of former Iron defender Lee Ridley, who played over 100 times for the club between 2000 and 2007, it was always going to be a stern test for Tony Daws' side.
And with goalkeeper Ewan Oxborough and forward Ty Sellars-Fleming on first team duty at Glanford Park for the game against Peterborough United, the side were a couple of bodies down for the encounter at West Street. In particular, Sellars-Fleming would have been missed having netted a hat-trick in the win over Bottesford Town on July 9th.
Winterton were to have their own hat-trick hero on the day, namely Josh Walker - who had notched an impressive 45 goals last season for the side in their Northern Counties East Premier Division campaign. Rangers will have been ecstatic to have kept him for the forthcoming season, but even more so that he seemed to be starting where he left off in front of goal.
The hosts took the lead after 20 minutes when Walker got the first of his first-half trebble, heading home from a pinpoint cross, before it matched with an equally impressive header 15 minutes later as another cross found his forehead.
Walker grabbed his hat-trick just before the interval before adding his and Winterton's fourth on 63 minutes.
The Iron were given chance for a consolation just a minute later when the hosts were adjudged to have fouled, with Tyler Edwards dispatching the penalty to make it 4-1.
Ryan Thompson would restore Winterton's four-goal advantage shortly after, before Grayson Giles reduced the arrears to make the final score 5-2.
Academy manager Tony Daws said: "It was a tough and very challenging match for us against a good and experienced Winterton Rangers team."