Main played at the highest youth level in Scotland with both the Rangers FC and Patrick Thistle FC. He played for a year in North Carolina on a soccer scholarship before an injury forced Main to return home. Upon returning home, Main completed his BA Sport Studies (Hons) degree at the University of Stirling in Scotland.
Stephen also began coaching and gained experience overseas before returning to the United States to continue coaching. During his time coaching, he has gained experience at the college, high school, premier and travel levels. Main was a part of an undefeated high school season in New Canaan as a coach and won numerous trophies at the premier and travel level.
He currently has a UEFA B license, NCAA advanced national and SFA level 3 qualifications.