Born in 1967, Jamie was reputed to be the Queen Mother’s favourite jockey, and had no shortage of admirers of his riding style during a colourful career in the saddle.

He hit the headlines in 1992 when he rode a record-equalling five winners at the Cheltenham Festival, including three in one day. The home of National Hunt was a lucky place for Osborne, whose festival wins included a Champion Hurdle, a Champion Chase, three Arkles and two Stayers’ Hurdles.

His most successful season came in 1996-97 when he came second in the jockeys’ championship, riding 131 winners. He had fruitful partnerships with several trainers, most notably Oliver Sherwood and Nicky Henderson.

Jamie took out his training licence in 1999 and it didn’t take him long to train his first Group winner in Milk It Mick by winning the Tattersall Stakes at Newmarket, followed by the Group 1 Dewhurst Stakes with the same horse. Windsor Castle Stakes winner Drawnfromthepast was Jamie’s first Royal Ascot success.

Toast Of New York winner of the UAE Derby (G2) at Meydan netted Jamie’s biggest prize of £722,892 and the same horse was beaten by just a nose in the 2014 Breeders’ Cup Classic – a horse purchased by Jamie himself.

“I’ve known Steve and Lewis for about 10 years now and I am excited to be training for this new syndicate – it looks like we could have some fun, and I really like the way The Numismatist is going.”

Some of Jamie’s notable winners

Raising Sand Challenge Cup, Ascot Heritage H’cap
Limitless Britannia Stakes, Royal Ascot Heritage H’cap
Field Of Dream Royal Hunt Cup, Royal Ascot Heritage H’cap
Toast Of New York UAE Derby, Meydan Group 2
Field Of Dream Bunbury Cup, Newmarket Heritage H’cap
Field Of Dream International Stakes, Ascot Heritage H’cap
Never Can Tell Cesarewitch, Newmarket Heritage H’cap
Geordieland Henry II Stakes, Sandown Group 2
Geordieland Yorkshire Cup, York Group 2
Drawnfromthepast Windsor Castle, Royal Ascot Listed
Moth Ball Rockingham Stakes, York Listed
Milk It Mick Dewhurst Stakes, Newmarket Group 1
Milk It Mick Tattersall Stakes, Newmarket Group 3
Toast Of New York winning the UAE Derby
Toast Of New York winning the UAE Derby
Never Can Tell winning the Cesarewitch
Never Can Tell winning the Cesarewitch
Milk it Mick winning the Gr.1 Dewhurst Stakes
Milk it Mick winning the Gr.1 Dewhurst Stakes


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