Robert Sly – more popularly known as Bob Sly – was born in the Gloucestershire village of Chedworth in 1808. He was unrelated to the jump jockey of the same name (1815-1874) who was active at the same time, even though they were both born in Gloucestershire. The latter rode as Robert Sly Junior in order to differentiate them
Based in Newmarket throughout his riding career, Bob Sly was a natural lightweight, weighing little more than five stone, a weight at which he remained all his life.
His major triumphs included the 1846 July Stakes on Sir Joseph Hawley’s filly Miami. Miami went on to win the following year’s Oaks but with Sim Templeman in the saddle.
Bob Sly never managed to ride a Classic winner although he did once finish second in the Oaks. Nonetheless, his services were very much in demand and he carved out a successful and lucrative career in the saddle and retired a rich man.
He lived in a grand house on Newmarket High Street, on the right-hand side heading up towards the racecourses. He occasionally trained horses, although he had no real need to financially.
He was the uncle of Frederick Clarke, the sixteen-year-old Danebury apprentice jockey who was fatally injured in a fall at Stockbridge in 1863.
Bob Sly lived to a good age. The end came on Wednesday, December 19, 1888, when he was seized with a fit whilst in his garden at Newmarket. He died almost immediately afterwards, aged 80. He was buried at Newmarket Cemetery on Saturday afternoon, 22 December.
He left the handsome sum of £8,154.
Bob died in the same week that jockey James Grimshaw perished (December 12).