Sir Henley is the Ice Hockey Coach at Royal Prep. He lives by the phrase "Work today, Win tomorrow".
He made his debut appearance in "Lord of the Rink". He first appears when the Ice Hockey team are practicing Ice Hockey and the Enchanted Ice Dancing class are practicing Enchanted Ice Dancing on the rink. After Sofia slides into the Hockey net and Hugo helps her up, Sir Henley decides that the rink sharing idea is not a good idea. After Flora says she will look for a new place for the ice dancing class, Sir Henley offers to let her have the ice for the rest of the day while he takes the Ice Hockey team for a run. When the team leaves, they remain unaware that Hugo has stayed behind. Later, he is joined by Hugo's father King Garrick as his assistant. Afterwards, both the hockey coaches notice Hugo's strange behavior. Later, after catching Hugo ice-dancing, the hockey team tells Garrick and Sir Henley that Hugo is unable to come to hockey practice because he is sick. When Hugo admits his passion for Enchanted Ice Dancing and leaves with Sofia, Garrick tries to stop him while the rest of the hockey team decide to see Hugo ice-dancing and Sir Henley joins them in going after him. He finds Hugo just in time to watch his duet for the ice-dancing recital and he is wowed by Hugo's talent. Since he has judged a dozen competitions in the past, Sir Henley finds Hugo's performance amazing.