She was from the first crop of foals sired by Honour and Glory, a Kentucky-bred stallion whose wins included the Breeders' Futurity Stakes and the Metropolitan Handicap.
[4] Caressing was consigned to the Keeneland sale as a yearling in 1999 and bought for $180,000 by the bloodstock agent Mike Ryan on behalf of Carl Pollard.
The overwhelming majority of his wins had come in claiming races, but he had enjoyed some top-level success in the 1970s with Honky Star, a racemare who won the Monmouth Oaks and the Cotillion Handicap.
[6] Caressing made her track debut in a maiden race over five and a half furlongs at Churchill Downs on July 2 and finished fourth of the eleven runners behind Madam Full Charge.
[6] On September 30 Caressing was moved up in class and distance for the Arlington-Washington Lassie Stakes over one mile at Arlington Park, she finished second to Thunder Bertie, beaten two and three quarter lengths.
[8] John Velazquez took over the ride from the injured Kuntzweiler when Caressing contested the seventeenth edition of the Breeders' Cup Juvenile Fillies, run that year at Churchill Downs on November 4.
Caressing raced in fifth place on the inside rail as Thunder Bertie set the pace before switching to the outside on the final turn.
[10] She made her belated three-year-old debut in the Grade III La Troienne Stakes over seven furlongs at Churchill Downs on May 3.
She finished sixth behind Exogenous in the Gazelle Handicap at Belmont in September[13] and third to Scoop in the Indiana Oaks at Hoosier Park in October.
[14] In November she ran fourth to Nasty Storm in the Churchill Downs Distaff[15] and sixth to Forest Secrets when starting a 29/1 outsider for the Falls City Handicap.