Conditioned for racing by two trainers, Leo Azpurua Jr and Terry J. Brennan, Certain had three wins and two second places in five starts at age two.
His three-year-old debut was an allowance win over The Groom is Red and Cryptodiplomacy, both owned by basketball coach Rick Pitino.
Certain's next race was the Fountain of Youth Stakes where he finished third by one length behind winner Vicar and second Cat Thief.
In 1999, Certain went to Oaklawn Park in Hot Springs, Arkansas to run in the Arkansas Derby, against the Breeders' Cup Juvenile Champion Answer Lively, and Valhol, a 30-1 long shot in the race.
Valhol won this race with Certain in second place and Answer Lively in fifth place; however, after the race, Valhol's jockey Billy Patin was accused of using or carrying an electrical stimulating device, after video footage from ESPN showed him dropping something on the ground and grounds keepers found a battery pack on the track.