Gypsum Daze Talent History
- 2025 - Chris Janson & Mackenzie Carpenter
- 2024 - Brian Kelley, Lauren Alaina, Travis Denning & Dakota Hale
- 2023 - Diamond Rio, Shane Profitt, Frankie Ballard, and Runaway June
- 2022 - The Marshall Tucker Band, The Cadillac Three, Nate Barnes & Michael Ray
- 2021 - Jimmie Allen, Pat Green & LOCASH
- 2020 - EVENT CANCELED DUE TO COVID-19
- 2019 - Scotty McCreery & The Lone Bellow
- 2018 - Randy Houser & Tracy Lawrence
- 2017 - Gary Allan & Swon Brothers
- 2016 - Hunter Hayes & Danielle Bradbery
- 2015 - Big & Rich, Jana Kramer & Cowboy Troy
- 2014 - Easton Corbin & Mark Chesnutt
- 2013 - LeAnn Rimes, Collin Raye & Imaj
- 2012 - The Nitty Gritty Dirt Band, Thompson Square & Gloriana
- 2011 - Joey+Rory, The Oak Ridge Boys & Eli Young Band
- 2010 - Rodney Atkins & Sarah Buxton
- 2009 - The Charlie Daniels Band & Little Big Town
- 2008 - JoDee Messina & James Otto
- 2007 - Darryl Worley, SheDaisy & Jamie O'Neal
- 2006 - Terri Clark & Western Underground
- 2005 - Sawyer Brown, Emerson Drive & Josh Turner
- 2004 - Clay Walker, Cowboy Crush & Jennifer Moorman
- 2003 - Honky Tonk Tailgate Party, Restless Heart
- 2002 - Pam Tillis & Rascal Flatts
- 2001 - Blackhawk & The Wilkinsons
- 2000 - Ty Herndon & Hal Ketchum
- 1999 - Michael Peterson
- 1998 - Dan Seals & Big House
- 1997 - Rick Trevino