Lord Derby died in June 1908 and his son Edward took over the family's racing and breeding operations. Trained by George Lambton at the Stanley House Stables in Newmarket, Suffolk, Swynford was a difficult horse to handle and in his only start at age two ran unplaced. An injury kept him off the track until 1910 when he made his three-year-old debut in the Epsom Derby. He finished well back in the Derby after being struck in the leg by another runner. Following a third in the St. James's Palace Stakes at Ascot Racecourse, Swynford then won the first of two consecutive editions of Ascot's Hardwicke Stakes. The colt went on to win the Liverpool Summer Cup and the third leg of the British Triple Crown, the St. Leger Stakes, somewhat fortuitously since "half the racegoers in England declared... [the race] had been thrown away by Danny Meher on Lemberg"