Despite the Dewhurst defeat, Rip Van Winkle started second favourite for the following season's 2000 Guineas largely due to his being still very unexposed and apparently the stable's first string as Johnny Murtagh had chosen him over Mastercraftsman.

On Derby day, he was again prominent in the betting but, despite Johnny Murtagh sticking with him and claiming he was the best horse he had ever sat upon, it was his stablemate Fame and Glory who went off marginal favourite just ahead of Sea the Stars.

In his next race at Sandown, back at a mile and 2, Sea the Stars was bidding to become the first horse to win the Guineas, Derby, Eclipse Stakes treble since Nashwan.

Poets Voice, the son of soft ground specialist Dubawi and winner of the Celebration Stakes, beat him in the last stride, ridden by Frankie Dettori, who won four out of his five races on the day at Ascot.

He sired 3 individual Group 1 winners: c = colt, f = filly, g = gelding It was reported on 31 July 2020 by Windsor Park Stud that Rip Van Winkle had died aged 14 after suffering a short illness.