Bobby Cruickshank first rose to prominence in reaching the semi-finals of the 1922 and 1923 PGA Championship, losing both times to eventual champion Gene Sarazen. In 1923, Cruickshank also lost in a playoff at Inwood Country Club in the US Open to Bobby Jones, a win that helped catapult Jones to a legendary career. He was also the runner-up in the 1932 U.S. Open. Cruickshank won 17 PGA Tour events and finished 16 times in in the top-10 at major championships in his career. Cruickshank was runner-up in the qualifying at the very first Metropolitan PGA Championship and went on to lose in the semifinals while playing out of the Progress Club in Westchester. His greatest year was 1927, when he won the Los Angeles and Texas Opens and finished as the leading money winner for the year. He last won on tour in 1936.