Winger signed in September 2019 having played in the National League for Chesterfield last season, making 25 appearances. A product of the academy at West Ham, where he played three senior games and represented England at Under 17, Under 18 and Under 19 level, he went on to make around 300 Football League appearances, over 100 of those for Bradford City, where he was part of the squad that reached the 2013 League Cup final and played in their League Two play-off final win against Northampton at Wembley. He also includes Charlton, Preston and Coventry among his former clubs.