Wintle began his career with North West Counties Football League side Alsager Town, following time in the academy at Stoke City,[3] and then joined Crewe Alexandra in January 2015, making his professional debut on 14 November 2015, coming on as a second-half substitute in a 2–0 League One defeat at Bradford City.

[6] After playing in the opening 10 games of the 2017–18 season, Wintle was injured in the 11th, a home defeat by Carlisle United on 23 September 2017, sustaining a stress fracture of his tibia that ruled him out "for months".

[8] After a difficult first half of the 2018–19 season that saw Crewe hover around the relegation zone, manager David Artell switched to a 4-3-3 formation which coincided with an upturn in both the team and Wintle's form.

[12] He made his Cardiff debut on 7 August 2021, coming on as a second-half substitute for Joe Ralls in a 1–1 draw against Barnsley.

[15] Wintle joined Blackpool on loan on 28 August 2021 for the remainder of the 2021–22 season,[16] making his debut in a 1–0 win over Fulham at Bloomfield Road on 11 September 2021.