Boland began his riding career in 1949 at Belmont Park in Elmont, New York. While still a sixteen-year-old apprentice, riding Better Self for owner Robert J. Kleberg Jr.'s King Ranch and trainer Max Hirsch, Boland earned the first stakes race win of his career on April 29, 1950 in the Gallant Fox Handicap at Jamaica Race Course. He went on to the Kentucky Oaks aboard Ari's Mona  then the following day rode Middleground to victory in the Kentucky Derby. Boland missed winning the U.S. Triple Crown series that year when he and Middleground finished second after a rough trip in the Preakness Stakes but then won the Belmont Stakes. In 1966 Boland won his second Belmont Stakes aboard Amberoid for trainer Lucien Laurin.
Widely respected by his peers, in 1959 Bill Boland received the George Woolf Memorial Jockey Award given to the North American jockey who demonstrates high standards of personal and professional conduct, on and off the racetrack.
Bill Boland retired from racing in 1969 and turned to training horses for a time. He was inducted into the United States Racing Hall of Fame in 2006.
- "William N. Boland". Racingmuseum.org. 2006-01-01. Retrieved 2018-12-09.
- "Fashions Own Pace at Jamaica Route: Young Bill Boland Handles King Ranch Horse Smoothly". Daily Racing Form at University of Kentucky Archives. 1950-05-01. Retrieved 2018-12-09.
- New York Times - June 17, 1956
- Sarasota Herald-Tribune - May 7, 1950
- The Wilmington, North Carolina Star-News - June 11, 1950
- Miami News - June 5, 1966
- The Spokane, Washington Spokesman-Review - February 3, 1959
| Jockeys' Guild President