A conditional jockey with Geoge Moore, James Roland Winterbotham made a perfect start to his career, winning on his first ride when the five-year-old Raiseabillion, trained by his boss, took the lead at the eighth flight and ran on well to beat the favourite Spritebrand by two lengths in the Turfcall Conditional Jockeys’ Handicap Hurdle at Sedgefield on November 6, 1987.
Raiseabillion was making his seasonal debut and went on to finish fourth on each of his next three outings. The last of those, at Edinburgh on December 21, was the only other occasion on which James rode him.
Raiseabillion won three races later that season when ridden by Micky Hammond, but James had few other opportunities despite having ridden a winner on his first mount in public.
His name was incorrectly shown as Winterbottom in the Chaseform annual following his Sedgefield success but is correctly shown as Winterbotham in the result of the Edinburgh race and also in the alphabetical lists of jockeys in both Ruff’s Guide and Horses in Training.