Eight of 29 entries reached the jump-off by riding without penalty over the 15-jump course designed by Show Jumping Hall of Famer Steve Stephens.
Earlier in the day, Tori Colvin and Laura Chapot took top honors in the 1.35 and 1.40 meter jumper classes.
Sinead Halpin and Joe Meyer are the first riders to win awards at this year's Rolex Kentucky Three-Day Event, presented by Land Rover.