Bay Middleton was a difficult horse to ride, and Lord Jersey had to beg the great jockey James Robinson (who had ridden five Derby winners) to try him.

He was in good company that day, beating Mendicant, the 1000 Guineas winner Destiny (by Sultan), and Magician (by Zinganee).

Bay Middleton won his second race with walk over, for £150, before taking the 2000 Guineas (Newmarket), defeated Elis and four others at a speed which was debated to have been a new record.

At the Grand Duke Michael Stakes, 21 horses withdrew to leave only Bay Middleton and St. Leger winner Elis.

Following this race, he was sold to Lord George Bentinck for 4000 guineas, who wished to run the colt in the Ascot Gold Cup.

However, this dream was never realized as Bay Middleton had physical problems with one of his forelegs, attributed to either the tendons or to a broken bone in his hoof.

[1] Due to his fine bloodlines and excellent track record, Bay Middleton covered some very good quality mares.

He also got four classic winners, in The Flying Dutchman, The Hermit, Andover, and Aphrodite, but many of his get had a tendency to roar, and he also seemed to pass on club-footedness to his offspring (possibly due to the Soothsayer blood in his veins).