Robin Benson competed in the men’s Dragon class at the 1960 Rome Olympic Games at Naples alongside David Ryder and A.J. Mooney (a previous Olympian), sailing Aletta to 12th place of 27 boats.

Alongside Mooney and Ryder, Benson had twice won the Duke of Edinburgh Cup against the best British yachtsmen, reflecting the high quality of the Irish Dragon class combination. The crew had developed a spinnaker drill that enabled them to set and hold the spinnaker faster than most rival crews. Despite measurement trouble at the start of the regatta requiring inside ballast, the crew performed creditably against strong international competition.