Stanley became a new boy at Eton in the Easter term of 1880 at the age of thirteen. His tutor was the Rev. S. A. Donaldson, and he settled in quickly as a successful sportsman. Winning the school pulling in 1883, and the school sculling and hurdles in 1884, he moved on to row for the Eton Eight (1884), when Eton won the Ladies' Plate at Henley (beating Radley by seven lengths). Stanley also played in the Oppidan and mixed wall games.