These awards are given to outstanding umpires who are recognized for his/her skills and dedication to umpiring for that year.
2024
- Umpire of the Year: Ken Saxer, Mid City Little League
- Umpire Service Award: Denis McGee, Allied Gardens Little League
2023
- Umpire of the Year: Robinaire Ruiz, Allied Gardens Little League
- Umpire Service Award: Jon Nathenson, North Park Little League
2022
- Rookie Umpire of the Year: Joshua Beail, San Carlos Little League
- Umpire of the Year: Colton Peterson, Mid City Little League
- Umpire Service Award: Ken Saxer, Mid City Little League
2021
- Rookie Umpire of the Year: Jake Robinson, San Carlos Little League
- Umpire of the Year: John Evans, Serra Mesa Little League
- Umpire Service Award: Mike Keller, San Carlos Little League
2020
- No Awards were given out due to the COVID-19 shutdown
2019
- Rookie Umpire of the Year: Jonah Baron, Patriot League
- Umpire of the Year: Brentt Hoover, San Carlos Little League
- Umpire Service Award: Jared Schlossberg, North Park Little League
2018
- Rookie Umpire of the Year: Clark Allen, La Mesa National Little League
- Umpire of the Year: Laura Sheppard, Sunshine Little League
- Umpire Service Award: Andy Carver, Serra Mesa Little League
2017
- Umpire of the Year: James Patocka, San Carlos Little League
- Umpire Service Award: Ric Castañon, Kearny Mesa Little League
2016
- Umpire of the Year: Ricky Mullberry, Lake Murray Little League
- Umpire Service Award: Olivier Wardendaar, Kearny Mesa Little League
2015
- Umpire of the Year: Jake Fenno, Allied Gardens Little League
- Umpire Service Award: Robinaire Ruiz, Allied Gardens Little League
2014
- Umpire of the Year: David Graham, Allied Gardens Little League
- Umpire Service Award: Sami Kern, Chollas Lake Little League
2013
- Umpire of the Year: Mark Tukeman, Patriot League
- Umpire Service Award: Ray Estrada, Lake Murray Little League
2012
- Umpire of the Year: Ric Castañon, Kearny Mesa Little League
- Umpire Service Award: Cliff Reed, Chollas Lake Little League
2011
- Umpire of the Year: Bob LaFave, San Carlos Little League
- Umpire Service Award: Rick Dempsey, Patriot Jr/Sr League
2010
- Umpire of the Year: Dan Hrigora, Mid City Little League
- Umpire Service Award: Mario Pappazi, San Carlos Little League
2009
- Umpire of the Year: John Perretta, North Park Little League
- Umpire Service Award: Raul Casillas, Chollas Lake Little League