Cash Run stepped out of her stable mate’s shadow for a brilliant performance in the 1999 Breeders’ Cup Juvenile Fillies at Gulfstream Park. The race was billed as a showdown between Chilukki, who was subsequently named Eclipse Award champion, and the accomplished Surfside, who like Cash Run, was part of trainer D. Wayne Lukas’ powerful stable. As a 32.50-to-1 longshot, Cash Run stole the show to win by 1 1/4 lengths for Satish Sanan’s Padua Stable while Chilukki and and Surfside were second and third, respectively. The victory was her first in stakes company and she added two more graded stakes victories to her resume at age three in her final season of racing. Cash Run caused a stir again in 2003 when she was sold for a world-record $7.1 million at auction.