 Pickering began his career with his hometown club, Blackburn Rovers, in 1959, signing professional forms on his 17th birthday.Pickering won three caps and scored five goals for England in 1964 during his Everton career.He made his international debut on 27 May 1964, against the United States, and scored a hat-trick in a 10–0 victory for Alf Ramsey's team.