He was moved to England in the late summer of his three-year-old season and subsequently emerged as one of the leading middle distance horses in Europe.
He was then moved up in class to contest Italy's most prestigious race for two-year-olds, the Group One Gran Criterium over 1500 metres at the San Siro Racecourse in Milan.
[4] After finishing second on his debut as a three-year-old, Orange Bay won the Group Two Premio Emanuele Filiberto over 2000 metres in Milan on 20 April, beating the British-trained Hobnob (later to win the Dante Stakes) by two lengths.
Orange Bay started 1/2 favourite for the Gran Premio d'Italia in Milan on 1 June, but finished second, beaten a short neck by Laodemonte.
In the Gran Premio di Milano two weeks later, Orange Bay was matched against older horses for the first time and finished fourth behind Star Appeal, Duke of Marmalade and Un Kopeck, with Dahlia in fifth.
[6] Eddery tracked Libra's Rib before taking the lead half a mile from the finish and maintained his advantage until the final furlong when he was overtaken by Bruni.
Orange Bay was then moved up to the highest level for Britain's most important weight-for-age race, the King George VI and Queen Elizabeth Stakes at Ascot in July.
Restrained by Eddery in the early stages, Orange Bay produced a sustained run in the straight and finished third, beaten a length and a head by Pawneese and Bruni.
[7] In September, Orange Bay was sent to Germany for the Grosser Preis von Baden but ran very poorly on heavy ground and finished unplaced behind the locally trained three-year-old Sharper.
In August, Orange Bay was brought back in distance for the Benson and Hedges Gold Cup over 10+1⁄2 furlongs at York Racecourse and finished third behind Relkino and Artaius.
He was then theoretically dropped in class for the Cumberland Lodge Stakes over 1+1⁄2 miles at Ascot in September a race which also attracted Meneval and the Epsom Derby runner-up Hot Grove.