UAEダービー
Osborne took out a trainer's licence in 1999. Based at The Old Malthouse stables in Upper Lambourn, he trains mainly on the flat with occasional runners over jumps. His first Grade 1 success as a trainer came in October 2003 with Milk It Mick in the Dewhurst Stakes. Royal Ascot wins include the Windsor Castle Stakes with Drawnfromthepast in 2007, the Royal Hunt Cup in 2014 with Field of Dream and the Britannia Stakes in 2016 with Defrocked (later renamed Limitless). In terms of prize money, the yard's biggest winner was Toast of New York, who brought in nearly £2 million from his 13 international starts. He won the 2014 UAE Derby at Meydan Racecourse in Dubai and later that year came second in the Breeders' Cup Classic on the dirt track at Santa Anita Park, beaten by only a nose.