Stanley Middleton was born on May 3, 1917. He won on his first ride in public, Pretty Obvious, at Newmarket on October 24, 1933.
He achieved his first big race success in the 1935 Royal Hunt Cup on Priok.
On June 29, 1938, he won the Cumberland Plate (then a big race) on Monk's Mead.
A video of his victory on Monk's Mead exists.