- 2015 Rusty Bumgardner, Kings Mountain, NC Second Base (2004 All Star Game MVP)
- 2016 Dal Beggs, Haines City, FL Infield (2002 Class-Major National MVP)
- 2017 Jason Kendrick, Naples, FL Outfield (2003 WSL Defensive Player of the Year)
- 2018 Mike Olive, Headland, AL Player/Manager (WSL Player Manager and now Director)
WSL Managers/Sponsors/Special/Meritorious
- 2015 John Daniels, Albertville, MN WSL Founder, Sponsor – Long Haul Trucking
- 2015 Joseph Doc Agostinelli, Niceville, FL Sponsor – Doc’s Softball
- 2017 Bob Shad, Cincinnati, OH Sponsor – EAP
- 2017 Gary Jost, Roseville, MN Player/Manager – Long Haul
- 2017 Cobbie Harrison, Louisville, KY Manager – R&D
- 2018 Mike Olive, Headland, AL Player/Manager – OI/Livingston
- 2018 Ray Hess, Ruther Glen, VA Manager – Plumbright
