2001: Two-year-old season

High Chaparral failed to make a winning debut, beaten by a short-head by Hot Trotter in a maiden at Punchestown on 30 September. A week later, he recorded his first victory when winning a maiden race at Tipperary by two and a half lengths.^[4] On his next start, High Chaparral was sent to England to run in the Group 1 Racing Post Trophy at Doncaster. He was considered the Ballydoyle second string, behind the odds-on favourite Castle Gandolfo. Ridden by the British veteran Kevin Darley, High Chaparral was held up in the early stages before producing a sustained run in the closing stages to beat his stable companion by three-quarters of a length.^[5]

2002: Three-year-old season

On his three-year-old debut, High Chaparral recorded a seven-length win in the Ballysax Stakes at Leopardstown on 14 April.^[6] A month later, he started at odds of 1/5 in the Derrinstown Stud Derby Trial and won by a length from In Time's Eye.^[7]

After winning both trials, High Chaparral was strongly fancied for the 2002 Epsom Derby and was made 7/2 second favourite. The strong favourite was his stable companion Hawk Wing, second in the 2,000 Guineas. Hawk Wing was selected by Mick Kinane, leaving the ride on High Chaparral to Johnny Murtagh. Among the other contenders was Bandari, who had won the Lingfield Derby Trial by over ten lengths. Murtagh held the colt up in the early stages, before moving up to take the lead early in the straight. He was soon challenged by Hawk Wing and from that point on the stablemates had the race between them. High Chaparral was never headed and won by two lengths. The O'Brien pair finished 12 lengths clear of Moon Ballad in third.^[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. Ridden by Mick Kinane, he took the lead in the closing stages and won from his stable companion Sholokhov, who had been his pacemaker.^[9]

High Chaparral was then off the racecourse for more than three months before running in the Prix de l'Arc de Triomphe at Longchamp in October. He was ridden by Mick Kinane and started 2.2/1 favourite against 15 opponents. He was always prominent and ran on strongly in the straight, but never reached the front and finished third behind Marienbard and Sulamani, beaten just over a length. Three weeks later, High Chaparral was sent to Arlington Park for the Breeders' Cup Turf. 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.^[10] After the race, Kinane described him as "all class".^[11]

2003: Four-year-old season

Contrary to the trend of retiring three-year-old champions, High Chaparral was kept in training at four, although he did not race until August. He then won the Royal Whip Stakes at the Curragh, beating Imperial Dancer by three-quarters of a length. 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.^[12]

In October, High Chaparral again started favourite for the Arc, this time going off at odds of 13/8 in a field of 13. He finished third, beaten more than five lengths by Dalakhani. 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. High Chaparral raced in fourth place before making his challenge in the straight. He appeared to have narrowly got the better of a sustained battle with Falbrav, but was then caught in the last stride by Johar. 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.^[13]

Notable progeny

c = colt, f = filly, g = gelding