As a two-year-old in 2008 he showed great promise as he won the Royal Lodge Stakes and was placed in the Racing Post Trophy and Prix La Rochette.

After racing towards the rear of the field he made progress on the outside, caught the leaders in the closing stages and won by a neck despite looking "green" (inexperienced) and hanging right near the finish.

Jukebox Jury missed the spring of 2009 and made little impact on his seasonal debut when he finished last of seven in the Prix Daphnis over 1800 metres at Longchamp on 22 June.

In August the colt was dropped back to Group 3 class for the Rose of Lancaster Stakes at Haydock Park and started 6/1 fourth choice in the betting.

[10] Jukebox Jury was moved up to Group 1 level when he was sent to Germany for the Preis von Europa over 2400 metres at Cologne on 27 September in which he again faced older opponents.

Eastern Anthem produced a sustained effort but Jukebox Jury prevailed by a nose with a gap of two and a half lengths back to Eliot in third place.

Ridden as usual by Ffrench he raced in second place before taking the lead in the straight but was overtaken in the final strides and beaten half a length by the six-year-old Champs Elysees.

[12] In early 2010, Jukebox Jury was sent to Dubai for the Sheema Classic at Meydan Racecourse on 27 March in which he finished fifteenth of the sixteen runners behind Dar Re Mi after fading badly in the straight.

After racing in second place behind Drill Sergeant, Ffrench sent Jukebox Jury to the front with half a mile left and the colt kept on well to win by almost four lengths from Nanton.

[14] After an absence of more than eleven months, Jukebox Jury returned in the Listed Fred Archer Stakes at Newmarket on 25 June in which he was ridden for the first time by Neil Callan.

[15] In the Glorious Stakes at Goodwood Racecourse a month later, Jukebox Jury partially recovered after being boxed against the inside rail to finish third, beaten a head and a neck by Drunken Sailor and Harris Tweed.

"[17] The Irish St Leger at the Curragh on 10 September attracted a field of six runners and Jukebox Jury, ridden by Johnny Murtagh started 4/1 second choice in the betting behind the odds-on favourite Fame and Glory.

Carrying a weight of 126 pounds (the second highest in the race) he finished in 20th place in the 23 runner field having sustained a hairline fracture to the cannon bone of his left foreleg.