| 1999 | Ted Robinson | Katie Starlight | M | Grays Starlight x Colonel Gunsmoke x Colonel Freckles | Paula Hunsicker | 865.0 |
| 2000 | Bob Avila | Paid By Chic | S | Smart Chic Olena x Oaklynn x Docs Oak | Jim Babcock/ Jim Dunn | 871.0 |
| 2001 | Ted Robinson | Katie Starlight | M | Grays Starlight x Colonel Gunsmoke x Colonel Freckles | Paula Hunsicker | 594.5 |
| 2003 | Ron Ralls | Cowgirls Are Smart | M | Smart Chic Olena x Sweet San Badger x Peppy San Badger | Jim Babcock & George Heckman | 594.0 |
| 2004 | Ron Ralls | A Chic In Time | S | Smart Chic Olena x Paula Tari x Tari Glo | Broken B Ranch | 582.5 |
| 2005 | Jon Roeser | Very Smart Remedy | S | Smart Little Lena x Remedys Response x Doc's Remedy | Anne M. Reynolds | 584.0 |
| 2006 | Andy Adams | Just Plain Cat | S | High Brow Cat x Shes Alenaglow Rio x Doc Olena | Robert Smith III | 871.5 |
| 2007 | Bob Avila | Light N Fire | S | Grays Starlight x Lenas Fine Freckle x Doc Olena | Rhodes River Ranch | 870.5 |
| 2008 | Russell Dilday | Topsails Rein Maker | S | Topsail Cody x Jameen Gay x Toby Gay Bar | Cantrelle & Dilday | 867.0 |
| 2009 | Russell Dilday | Topsails Rein Maker | S | Topsail Cody x Jameen Gay x Toby Gay Bar | Cantrelle & Dilday | 884.0 |
| 2010 | Randy Paul | Smokeelan | S | Elans Playboy x Smart Little Smokee x Smart Little Lena | Jill Smiekel-George | 875.5 |
| 2011 | Russell Dilday | Topsail Rein Maker | S | Topsail Cody x Jameen Gay x Toby Gay Bar | Cantrelle & Dilday | 874.5 |
| 2012 | Ron Emmons | Olena Oak | S | Smart Chic Olena x Fritz Oak E Doakie x Docs Oak | Mel Smith & Nichole Scott | 885.5 |
| 2013 | Ron Emmons | Olena Oak | S | Smart Chic Olena x Fritz Oak E Doakie x Docs Oak | LaDona Emmons & Nichole Scott | 874.0 |
| 2014 | Boyd Rice | Oh Cay N Short | S | Oh Cay Quixote x Bit Of Shorty x Shorty Lena | Boyd Rice | 877.5 |
| 2015 | Corey Cushing | PRF Spoonful Of Gold | S | Hes A Peptospoonful x Sons Miss Sprat x Sons Rushette | Cathy Corrigan Frank | 889.0 |
| 2016 | Clayton Edsall | Skeets Oak Peppy | G | Skeets Peppy x Oak Ill Be x Ill Be Smart | Clayton Edsall | 883.0 |
| 2017 | John Swales | Heza Diamond Spark | S | Diamond J Star x Hickorys Holly Cee x Doc's Hickory | 7 P Ranch | 874.0 |
| 2018 | Kelby Phillips | Hickory Holly Time | S | One Time Pepto x Hickorys Holly Cee x Doc's Hickory | DT Horses | 890.5 |
| 2019 | Corey Cushing | Sonita Lena Rey | G | Dual Rey x Sonita Lena Chick x Smart Chic Olena | Sheri Jamieson | 877.0 |
| 2020 | John Swales | Metallic Cat Rose | M | Metallic Cat x Teletrona x Little Trona | Jerry and Nicole Myer | 878.5 |
| 2021 | Shane Steffen | Gunna Be A Smartie | M | Very Smart Remedy x Gunna Be Mine x Gunna Smoke | McSpyder Ranch | 894 |
| 2022 | Corey Cushing | Hott Rod | S | Hottish x Sugars Smart Kitty x High Brow Cat | Lynne Wurzer | 893 |
| 2023 | Phillip Ralls | Call Me Mitch | S | Metallic Cat x Miss Hickory HIll x Docs Hickory | Estelle Roitblat Living Trust | 902 |
| 2024 | Shawn Hays | MoonshineAndTwoAdvil | G | Metallic Cat x Little Short Stuff x Shorty Lena | Angela Massey | 885.5 |
