Trained by Graham Motion, Ring Weekend broke his maiden at Gulfstream Park in February 2014 before going wire to wire in the $350,000 Tampa Bay Derby (G2). He then finished out his 3-year-old year with wins in the $300,000 Saranac Stakes (G3) at Saratoga and the $500,000 Hill Prince (G3) at Belmont.
He started his 4-year-old season with a dynamite victory in the $400,000 Frank E. Kilroe Mile (G1) at Santa Anita before being sidelined for the rest of the year due to a foot abscess.
Off a long layoff, the son of Tapit ran huge to finish second in the $250,000 Dixie Stakes (G2) on Preakness Day in 2017. He then set a new course record in the $250,000 Bernard Baruch Handicap (G2) on closing day of the Saratoga meet before ending the year with a win in the $200,000 Seabiscuit Handicap (G2) at Del Mar.
Ring Weekend was retired in 2018 after winning an allowance race at Gulfstream Park. He spent some time eventing with Olympian Phillip Dutton before moving to Old Friends in Kentucky in 2021.