Winling, a New Orleans native, was an outstanding athlete during his time on the Hill. "Wing" excelled in four sports; football, basketball, baseball and boxing. His exploits in the 28-7 win over Loyola (La.) during the 1921 season, where Harold ran the ball for 127 yards, averaging seven yards a carry, and his multiple three-touchdown games are legendary. Even against the much bigger opponents like LSU, he performed well. He was captain of the 1921 and ’22 football teams and was a key member of the 1920 gridiron squad that went 6-2. Whether at end or in the backfield, Wing’s athletic ability was on display. As a four-year letterman in basketball, Winling was known as a tough defensive guard with a soft shooting touch. He captained the 1923 Bagers to victories over Tulane and LSU. In baseball, he could play anywhere on the field. His career on the diamond was highlighted by wins against LSU, Tulane and some professional ball clubs. His personal highlight was a home run off Major League pitching versus the St. Louis Browns. Wing had a career best .310 batting average for the Badgers in 1920. He was also President of his Senior Class.