2013: two-year-old season

Fascinating Rock made his racecourse debut in a maiden race over one mile on very soft ground at Leopardstown Racecourse on 26 October. He finished fifth of the ten runners, ten and a half lengths behind the winner Adelaide.

2014: three-year-old season

On his three-year-old debut, Fascinating Rock started at odds of 9/1 in an eight-runner maiden over ten furlongs at Leopardstown on 30 March and won by a length from the Aidan O'Brien-trained Adjusted.^[4] At Navan Racecourse two weeks later the colt was moved up in class for the Group Three Ballysax Stakes and started 5/2 second favourite behind the Jim Bolger-trained Answered. He produced a strong run on the outside in the straight to take the lead a furlong out and won by two and a half lengths from Answered.^[5] The colt's next race was the Derrinstown Stud Derby Trial over ten furlongs at Leopardstown on 11 May, for which he started favourite against five opponents headed by the Beresford Stakes winner Geoffrey Chaucer. After being held up at the rear of the six runner field he finished strongly but failed by a head to overhaul the John Oxx-trained Ebanoran. He had been bumped by the "winner" in the closing stages and after a stewards' enquiry the placings of the first two finishers were reversed and the race awarded to Fascinating Rock.^[6]

On 7 June, Fascinating Rock was sent to England to run in The Derby and started at odds of 12/1 in a field of sixteen runners. After being badly hampered approaching the straight he never looked likely to mount a challenge and finished eighth, more than eleven lengths behind the winner Australia. Fascinating Rock faced Australia again in the Irish Derby at the Curragh Racecourse three weeks later but made no impact and finished last of the five runners.

2015: four-year-old season

Fascinating Rock began his third season in the Listed Heritage Stakes over one mile at Leopardstown on 15 April. Starting the odds-on favourite on his first start for almost nine months, he recovered from a poor start to win by one and three quarter lengths from the five-year-old mare Alive Alive Oh.^[7] On 4 May the colt started 2/5 favourite for the Group Three Mooresbridge Stakes at the Curragh against three opponents headed by the 2011 Dewhurst Stakes winner Parish Hall. He raced in second before taking the lead approaching the final furlong and won by one and three quarter lengths from Parish Hall.^[8] In a strongly-contested Tattersalls Gold Cup at the same course three weeks later he was beaten a neck by Al Kazeem, with Postponed third, The Grey Gatsby fourth and Parish Hall fifth.

After a three-month break, Fascinating Rock returned for the Winter Hill Stakes at Windsor Racecourse in England on 29 August. He started the 6/5 favourite but finished fifth of the eight runners behind the Godolphin three-year-old Racing History. In the Enterprise Stakes over one and a half miles at Leopardstown on 12 September the colt started second favourite behind Answered in a field which also included the one time Derby favourite John F Kennedy. After racing in third place, he took the lead in the last quarter mile and drew away from his rivals to win by six lengths from the gelding Panama Hat.^[9]

On 17 October Fascinating Rock was sent to England for the third time and started at odds of 10/1 for the Group One Champion Stakes over ten furlongs at Ascot Racecourse. The Irish Derby winner Jack Hobbs started favourite ahead of Found, whilst the other runners included Vadamos (Prix Niel, Oettingen-Rennen), The Corsican (Arc Trial), Ribbons (Prix Jean Romanet), Racing History, Sumbal (Prix Greffulhe), Air Pilot (International Stakes) and Tullius (Sandown Mile, York Stakes). Smullen restrained the colt towards the middle of the thirteen runner field as the pacemaker Maverick Wave made the running from Jack Hobbs. He began to make progress in the straight, overtook Jack Hobbs inside the final furlong and held off the late challenge of Found to win by one and a quarter lengths. Jack Hobbs finished third ahead of Racing History and Air Pilot. After the race, Weld said "He likes this ground and I've thought this race would suit him for a while. I was very impressed with the way he won at Leopardstown and after that we stuck with the original plan, which was always today. The way he was ridden today was also always the plan, from off the pace. I had a fair idea they would go a pretty good gallop so I told Pat to take him time and hunt away as I knew the horse would come home for him. He'll be a better five-year-old as well."^[10]

2016: five-year-old season

Fascinating Rock began his third season in the Mooresbridge Stakes at the Curragh on 2 May. He was made the 11/10 favourite, but was unable to quicken in the closing stages and finished third behind Found and Success Days. Three weeks later he faced Found and Success Days again as he made his second attempt to win the Tattersalls Gold Cup. Starting the 9/4 second favourite he tracked the leader Success Days before taking the lead two furlongs out. He drew away in the closing stages to win by three and three quarter lengths from Found.^[11]