Scott Middlemass, son of Cive Middlemass who played for Workington and managed Carlisle  was first associated with Exeter City when he unsuccessfully sought a youth contract in 1988. He is understood to have returned six or seven years later for a second trial having gained experience in non-league football.

Unsuccessful in his efforts to become a trainee with Exeter City ahead of the 1988/89 season  he found a place at Carlisle United - where his father Clive was first-team manager -   but soon switched to Preston North End to complete his two-year training. After seeking trials with other professional clubs , he went into non-league with Ashton United, Macclesfield and Chorley and at some stage had a second try-out for Exeter City in a reserve game during 1994/95.

Later playing for a variety of non-league clubs in the north of England, he had spells playing for the reserves at Cambridge United and Doncaster Rovers before playing in China, the United States and Norway ahead of signing for Scarborough. Moving to the United States on a permanent basis in 2001, he coached youth soccer and worked at an athletic academy in New Jersey.