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.

2025: Brad Qualls, CAA Patriot High School
2018: Mike Costello, CAA Wakefield Country Day School
2017: Kevin Cole, CMAA Chesapeake Public Schools and John Williams, CAA Ocean Lakes High School
2016: Steve Heon, CAA Western Albemarle High School and Chris Rollison, CAA Hermitage High School