Tony Cunningham earned his 100th career Quarter Horse Victory on Saturday at Horseshoe Indianapolis

© Coady Media

By Tammy Knox

SHELBYVILLE, IN–JUNE 27, 2026–Tony Cunningham has been a major player in Indiana pari-mutuel Quarter Horse racing since its inception in 1997. The Michigan native has competed every year since that time. Many of his wins have been secured in the Hoosier State, and now a special milestone can be added to his credentials. Cunningham scored two wins Saturday, June 27 and earned his 1,000th career Quarter Horse victory at Horseshoe Indianapolis.

Cunningham came into the day two away from the milestone. He earned a victory with Apollitical Fast in the seventh race, one of the trials for the Heartland Futurity. The Apollitical Blood filly was ridden to victory by L. Daniel Martinez for owner-breeder Brian Gunder.

Cunningham was back in the winner’s circle for the 12^th race, another trial for the Heartland Futurity. No photo finish was needed as Kissin Jessy and Martinez, his primary rider, pulled away from the field to win by a length at the wire to secure the milestone.

“I couldn’t do it without everybody else on our team,” admitted Cunningham. “Especially my wife (Lisa) who puts up with me being on the road so much. She takes care of everything at our farm in Michigan while I’m down here. And Salvadore, who has been with me for a lot of years, handles everything at the track when I am home. It’s a great feeling to get this (milestone).”

The milestone also had extra meaning to Cunningham. Kissin Jessy is owned by Pam Hann, Ruby Huggins, and his wife Lisa. The freshman daughter of Kiss My Hocks was making her third career start and earned her first career win for the Cunningham barn. Kissin Jessy was a $78,000 purchase for the connections last fall at the Heritage Place September Yearling Sale.

In addition to his stellar Quarter Horse career, Cunningham is also training Thoroughbreds at Horseshoe Indianapolis. He has an additional 69 wins in that category.

Cunningham has been training Quarter Horses since 1992. His best year to date was 2023 when he scored his second of three million dollar seasons and had 41 wins on the year. He was leading trainer at Horseshoe Indianapolis in both 2023 and 2024 and holds records for most Quarter Horse owner titles (3) and is the track’s all-time leading Quarter Horse owner. He has been among the track’s top five trainers each year since the inaugural season in 2003

The 24th season of live Thoroughbred and Quarter Horse extends through Friday, November 13. For more information on racing at Horseshoe Indianapolis, visit www.caesars.com/horseshoe-indianapolis/racing or find details on social media @HSIndyRacing.

About Horseshoe Indianapolis
Located just minutes from Indianapolis in Shelbyville, Ind., this one-of-a-kind property has wall to wall excitement on the 105,940 square foot gaming floor, featuring more than 1,600 slots and 72 table games along with a state-of-the-art World Series of Poker Room containing 20 tables. In addition, Horseshoe Indianapolis offers the only live Thoroughbred and Quarter Horse racing in the state showcased on a one-mile dirt racecourse and a seven-eighths mile turf course. Simulcast and sports wagering is offered year-round at Caesars Race & Sportsbook. Please visit www.caesars.com/horseshoe-indianapolis for more information and find Horseshoe Indianapolis on Facebook, Twitter, and Instagram.

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