With more than $739,407+ in cow horse earnings, Cayley Wilson found success in his training program, a venture that started in Canada and moved to Texas. Cayley began his cow horse program in Abbotsford, British Columbia, where he earned multiple premier event titles, both within Canada and the United States.
 
After his move to Texas in June of 2021, Cayley earned 3rd place in the 2022 NRCHA Open Snaffle Bit Futurity® and was Reserve Champion in the Intermediate Open Futurity aboard Nothing But Blu, owned by Alicia Bolls. He and this prestigious Stallion also had great success earlier in the year, winning the 2022 Intermediate Open division at the Dom Conicelli Memorial Eastern Derby, presented by MARS Equestrian™. Today, the pair have amassed over $134k to Nothing But Blu's lifetime earnings and are still going strong.
 
Cayley has also had success in the Cutting pen. Most recently, at the NCHA Futurity in 2022 he rode Benjie Frost’s Little Lucey Lue, trained by Ascencion Banuelos, to advance to the semi-finals. Cayley also bought, trained and showed Hot Frosted Cat for owner Bonnie Pearson to the Open Championship at the Black Elk Cutting Futurity in Ponoka Alberta in 2020 and rode CR Wood She Be Blu to reserve Championship at the Canadian Spectacular Cutting Futurity in 2020.

The latest success was found in October of 2023, where Cayley qualified 3 of his 6 entries back to the NRCHA Open division Snaffle Bit Futurity Finals. These 3 horses were Rebell for owner Sandy Allen, Hip Hip Rebel Rey for owner Kathy Gentry and Kual outlaw for Michelle Cannon.  Cayley finished 2023 strong, ranking 1st in the Nation in the Open Hackamore piloting Shine Like A Dime, for owner Michelle Cannon.