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

2025: Brad Qualls, CAA Patriot High School
2024: Michael Payne, CAA, Gar-Field
2024: Carol Callaway, CMAA, Washington-Liberty
2024: Derek Farrey, CAA, Loudoun County Public Schools
2023: Matt Pearman, CAA, Monticello
2023: Lisa Corprew, CAA, Bayside
2022: Tim Leach, CAA, Spotswood
2022: Kevin Adams, CAA, Varina
2021: David Rhodes, CAA, Virginia Beach City Public Schools|
2021: Scott Morris, CAA, Fluvanna County
2021: Tom Dolan, CAA, Virginia High School League
2020: Greg Wade, CAA, Radford
2020: Dan Jones, CMAA, King William
2020: Trevor Coleman, CAA, Honaker
2019: Ted Salmon, CAA, Retired
2019: Rick Lilly, CAA, Highland Springs
2018: Mike Costello, CAA Wakefield Country Day School
2017: Kevin Cole, CMAA Chesapeake Public Schools
2017: John Williams, CAA Ocean Lakes High School
2016: Steve Heon, CAA Western Albemarle High School 
2016: Chris Rollison, CAA Hermitage High School
2015: Derek Farrey, CAA, Tuscarora