Maryland’s Winningest High School Football Coaches: The 10 Active Legends You Need to Know

From DeMatha’s Bill McGregor to Broadneck’s Rob Harris, these coaching giants have built dynasties, defined eras, and stacked victories across decades of Maryland high school football

DeMatha's Bill McGregor is far and away the winningest active Maryland high school football coach, at his current school, with 323 victories in 36 years, despite being away from the program for eight seasons in between his two stints with the Stags. / Troy Queen

Coaching consistency and on-field success go hand in hand in high school football. It should come as no surprise, then, that the winningest active coaches in Maryland, ranked solely by their coaching records at their current schools, lead many of the state’s top teams.

DeMatha's Bill McGregor Tops the Field with 323 Wins with the Stags

Bill McGregor, in his second stint at DeMatha, leads the pack with 323 wins during a stellar 36-year career. His win total ranks second overall in Maryland history, trailing only Bob Milloy’s 405. McGregor is one of only four Maryland coaches to ever top 300 wins, along with Milloy, John Harvill (Gaithersburg), and Doug DuVall (Wilde Lake).

Linganore's Rick Conner and River Hill's Brian Van Deusen Have Each Surpassed 200 Wins

Second on the active list is Rick Conner, who took Linganore to a state final in his first season as the program’s head coach. The Lancers have returned to the state finals 10 times since. Conner and Steve Crounse are the only coaches on the list who have been head coaches elsewhere. Conner’s career total of 230 victories places him 14th all-time in Maryland.

Brian Van Deusen rounds out the top three with 220 wins at River Hill, a program he took over from his father, Don, the school’s first head coach. Brian Van Deusen’s win total ranks him 16th in Maryland history.

Kurt Stein at Oakdale (102 wins) and Kyle Schmitt at Archbishop Spalding (90) are just outside of the Top 10.

Here is the list of the winningest active coaches, based on wins only at their current school:

Coach	School	Record	Years Active
Bill McGregor	DeMatha	323-53-3	1982-2010, 2019-2025
Rick Conner	Linganore	221-55	2002-2025
Brian Van Deusen	River Hill	220-67	2000-2025
Reggie White	Milford Mill	185-64	2003-2025
Dan Paro	Georgetown Prep	179-86	1997-2025
Steve Crounse	Patuxent	153-57	2002-2016, 2022-2025
James Monroe	Lake Clifton/Reach	150-47	1995-2025
Mike Nesbitt	Paint Branch	135-55	2007-2025
Tommy Green	Eleanor Roosevelt	127-51	2008-2025
John Kelly	Quince Orchard	121-11	2014-2025
Rob Harris	Broadneck	117-34	2011-2025

*Records compiled by Sheldon Shealer as part of the MD History project.