Stephen Pears started his career at Manchester United as an understudy to Gary Bailey. However, Pears struggled to displace him and break into the first team. During the 1983–84 season, in order to gain match practice, he was sent to Middlesbrough on loan where he became a fan favourite. Middlesbrough attempted to sign him permanently but the club failed to raise the £80,000 fee. However, Middlesbrough made a second attempt to sign Pears and he transferred to the club permanently in 1985.