In September 2000, he was consigned by the Mountain View Stud to the Tattersalls sales, where he was bought for 270,000 guineas by Dermot "Demi" O'Byrne on behalf of Michael Tabor's Coolmore organisation.

High Chaparral failed to make a winning debut, beaten by a short-head by Hot Trotter in a maiden at Punchestown on 30 September.

[5] On his three-year-old debut, High Chaparral recorded a seven-length win in the Ballysax Stakes at Leopardstown on 14 April.

Hawk Wing was selected by Mick Kinane, leaving the ride on High Chaparral to Johnny Murtagh.

[8] Three weeks after his win at Epsom, High Chaparral reappeared in the Irish Derby at the Curragh, for which he started as the 1/3 favourite.

He was held up in the early stages before producing what The Guardian's correspondent described as an "irresistible surge" to take the lead in the final furlong and win by one and a quarter lengths from With Anticipation.

Four weeks later, he won a rough race for the Irish Champion Stakes at Leopardstown, beating Falbrav by a neck with Islington third and the King George winner Alamshar fourth.

On his final start, he returned to the United States to attempt to become the first horse to win two runnings of the Breeders' Cup Turf.

The result of the three-way photo-finish was a dead heat for first place between High Chaparral and Johar, with Falbrav a head back in third.

[16] During the 2005 Northern Hemisphere winter, High Chaparral was a shuttle stallion at Windsor Park Stud in New Zealand.