The Outstanding Service Award is presented to someone in the VIAAA who has made significant contributions to the professional of Athletic Administration or to the VIAAA.

2018
Mike Costello, CAA Wakefield Country Day School

2017
Kevin Cole, CMAA Chesapeake Public Schools
John Williams, CAA Ocean Lakes High School

2016 
Steve Heon, CAA Western Albemarle High School 
Chris Rollison, CAA Hermitage High School