Home/Ipswich Cup marks 160 years as ground-shaking Festival of Horsepower returns/The first official Ipswich Cup was said to have been raced in 1866, with the Cup itself, a magnificent trophy, being made and transported from England for the special event. The first official Ipswich Cup was said to have been raced in 1866, with the Cup itself, a magnificent trophy, being made and transported from England for the special event.