William J. Stewart, Jr. Award for Outstanding High School Official

Bill Stewart Jr. was coach of football, hockey and baseball at Boston English and a high school and college official in all three sports. He is a member of the High School Coaching Hall of Fame.

Prior to 2000: Bill McDonald, Patrick Santin, Bill Leaneus, Bill McDonald, Peter Brady, Paul Lyons, Paul Howard, Al Sheehan, Tom English, Bill Lanagan, George Murphy, Bob Donovan