Flemensfirth did not appear on the racecourse until the September of his two-year-old season, when he won a Nottingham maiden race "smoothly"[3] by three lengths.

After finishing unplaced in the Prix du Jockey Club and the St. James's Palace Stakes he was rested for an autumn campaign.

He returned to Longchamp for the Arc meeting, where he led all the way to win the Group 2 Prix Dollar by half a length from Volochine.

[6] A month later he travelled to Italy to land odds of 1–2 in the Premio Roma, defeating the German mare Hollywood Dream by a neck.

By the time he appeared again in the 1997 Dubai World Cup, Flemensfirth had not lost a race for almost two years, but he was always struggling on the dirt surface, and came home last of the ten finishers behind Singspiel.