Duel Derby winner Shahrastani has been put down because of bad health aged 28.
The son of Nijinksy is most famously remembered for his defeat of Dancing Brave in the 1986 Epsom Derby when they majority of the racegoers believed Dancing Brave should have won that race.
However Shahrastani proved that Epsom win was no fluke as he romped away with the Irish Derby a few weeks later at the Curragh and while his career finished in disappointment, he would go onto have a productive career at stud siring 13 black type winners including French Group 2 winner Rifapour.
Stud owner Wayne Hutchinson said: “He was starting to go down in health so it was felt prior to Christmas it had to be dealt with so he had no suffering. It’s a sad thing but he had a very good innings and spent a good ten years with us.
“He probably didn’t get the recognition he deserved as a stallion but when he was exported to Japan he went off the breeders’ radar. He passed away peacefully.