After being purchased, and determined to be healthy enough to attempt a racing career, Da Hoss was taken to Turf Paradise in Phoenix, Arizona.

The horse he finished second to in the GII Swaps Stakes was that year's Kentucky Derby and Belmont winner, Thunder Gulch.

After Da Hoss won by three parts of a length, Dickinson entered him in the 1998 Breeders’ Cup Mile.

It is likely the horse would have been refused entry had he not won the allowance, as the committee wanted to avoid another incident like Ricks Natural Star.

[5] Dickinson wanted Gary Stevens to ride Da Hoss, but the jockey's agent, Ron Anderson, had committed him to another horse.

After a delayed start caused by several horses not wanting to load in the gate, Da Hoss settled in sixth in the early stages of the race, allowing the speed horses to battle it out in front of him, and was among those closing in on Favorite Trick heading to the final straight.

It seemed that Da Hoss would finish second, but he put his nose back in front just before the wire to take his second Breeders' Cup Mile to the call of announcer Tom Durkin.