Ian Benstead was born on May 20, 1935. He served his apprenticeship with his father, Christopher Benstead, who trained under Pony Turf Club Rules. Between 1950 and 1953 Ian rode under PTC Rules and was champion apprentice in 1951 with 21 winners.
He rode under National Hunt Rules between 1954 and 1956 and had one win, on September 25, 1954, when his mount Ramastra, trained by his father, won the Hartland Handicap Hurdle at Newton Abbot by three lengths. Their victory was well deserved, for they had finished second twice, at Buckfastleigh and Wincanton, already that season.
Ian took out a trainer’s licence in 1957, based at Four Fields Farm, Headley, in Surrey, combining training with stock farming. He relinquished his licence in 1966.