He rode for and was apprenticed by T.P. Hayes, the owner of Donerail.
He went on to ride for another two decades during which time he had two mounts in the Kentucky Derby, winning in 1906 aboard Sir Huon and finishing second on Governor Gray in 1911. Recognized for his ability to handle inexperienced two-year-olds, Roscoe Troxler rode at tracks across the United States as well as the 1916-1917 winter meet at Agua Caliente Racetrack in Tijuana, Mexico where he had victories with nineteen of his fifty-seven mounts for a 33% winning percentage. Roscoe Troxler retired from riding in 1920 after seriously injuring himself in a fall at Pimlico Race Course.
He then worked as a trainer until retiring in 1953.
, he enjoyed his best success with El Mono in 1948 at Florida"s Hialeah Park Race Track. Thoroughbred racing was a way of life for Roscoe Troxler and in his nineties he was still working six days a week as a steward"s aide at racetracks in the South Florida metropolitan area.
He retired in May 1976, a few weeks before his ninety-third birthday and died at his home in Miami on July 7.