Sydney Bailey started racing with the South West Ham Rovers CC at the age of 18 before a move, in 1907, to the Polytechnic Club. He won the 10-mile race, for the Surrey Cup, at Kennington Oval in 1909, and the following year won the 10-mile point-to-point race for the Penrose Cup at the Southern Championship at Herne Hill, beating the 1908 Olympic silver-medalist Charles Denny into second place. Also in 1910, Bailey finished third in the motor-paced race at the World Championships in Brussels. In an attempt to set new amateur motor-paced records at Canning Town that year, he set every record from 440 yards to seven miles and probably would have set more had there not been a fault with his pacing vehicle. Bailey also broke Leon Meredith’s one and 10-mile motor-paced cinder track records at Fallowfield, Manchester, in 1913. After the War, Bailey raced as a professional, and in 1924, at the age of 38, broke the professional motor-paced records for two, four and six miles, again at Fallowfield.