Goalkeeper Winterbottom was an unused substitute for Liverpool's first team in the quarter-finals of the Carabao Cup against Aston Villa on 17 December 2019. Winterbottom had joined the club from Blackburn Rovers nine months earlier. Brentford signed the keeper for their B side on a two-and-a-half-year contract on 29 January 2021. Brentford B play only friendlies and for the first half of 2023/24 he was loaned to Welling United of the National League South, making fourteen appearances. At the end of the spell he signed a one year contract extension with Brentford B and was loaned to Fylde, of the National League, for 2024/25.