Richard Hilleary led Woodbridge to its most dominating era in wrestling. During his 14 years (1984-1998) as Woodbridge’s head coach he produced six Commonwealth/Cardinal District championships (1987, 1988, 1989, 1990, 1991 and 1998), four Northwest Regional championships (1987, 1988, 1990 and 1991) and led Woodbridge to two team Virginia State Duals finals (1990 and 1991). In addition, he coached a variety of other sports at Woodbridge and as head baseball coach in 1994 led Woodbridge to the Commonwealth District championship. 

Hilleary’s regional titles represent four of the five won all-time by Woodbridge, and his teams won six of the eight all-time district titles. The two appearances in the Virginia State Wrestling Team Dual finals are the only appearances in the school’s history. He also produced two state champions: Brian Shaffer in 1986 at 132 pounds and Daryk Moistner in 1991 at 171 pounds. 

In 1997-98, which was his final season coaching at Woodbridge, his team went 31-1 and set the single-season school record for victories. During that season, Woodbridge took first at the Norfolk Sports Club Titan Wrestling Classic and another at the 10-team Viking Wrestling Tournament. Hilleary was selected as the Washington Post 1998 Wrestling All-Met Coach of the Year. The following year he was named the 1999 Virginia High School Coaches Association Coach of the Year. 

Hilleary coached 37 individual district champions, 25 individual regional champions and nine third-place state finishers and three state runners-up with Greg Mincey in 1986, Reggie Mincey in 1988, and Jim Dutrow in 1996. His wrestlers also earned 33 All- State and 12 All-Met honors while Shaffer, Moistner, and Dutrow were named First-Team All-Met by the Washington Post. 

In his overall multi-school coaching career, Hilleary’s teams totaled 325 wins to rank fourth all-time in Virginia High School League history.