Crosby had an interest in sports. In the 1930s, his friend and former college classmate, head coach Mike Pecarovich appointed Crosby as an assistant football coach. From 1946 until his death, he owned a 25% share of the Pittsburgh Pirates. Although he was passionate about the team, he was too nervous to watch the deciding Game 7 of the 1960 World Series, choosing to go to Paris with Kathryn and listen to its radio broadcast. Crosby had arranged for Ampex, another of his financial investments, to record the NBC telecast on kinescope. The game was one of the most famous in baseball history, capped off by Bill Mazeroski's walk-off home run. He apparently viewed the complete film just once, and then stored it in his wine cellar, where it remained undisturbed until it was discovered in December 2009. The restored broadcast was shown on MLB Network in December 2010.
Crosby was also an avid golfer, and in 1978, he and Bob Hope were voted the Bob Jones Award, the highest honor given by the United States Golf Association in recognition of distinguished sportsmanship. He is a member of the World Golf Hall of Fame. In 1937, Crosby hosted the first 'Crosby Clambake' as it was popularly known, at Rancho Santa Fe Golf Club in Rancho Santa Fe, California, the event's location prior to World War II. Sam Snead won the first tournament, in which the first place check was for $500. After the war, the event resumed play in 1947 on golf courses in Pebble Beach, where it has been played ever since. Now the AT&T Pebble Beach Pro-Am, it has been a leading event in the world of professional golf.
Crosby first took up golf at 12 as a caddy, dropped it, and started again in 1930 with some fellow cast members in Hollywood during the filming of The King of Jazz. Crosby was accomplished at the sport, with a two handicap. He competed in both the British and U.S. Amateur championships, was a five-time club champion at Lakeside Golf Club in Hollywood, and once made a hole-in-one on the 16th at Cypress Point.
Crosby was a keen fisherman especially in his younger days but it was a pastime that he enjoyed throughout his life. In the summer of 1966 he spent a week as the guest of Lord Egremont, staying in Cockermouth and fishing on the River Derwent. His trip was filmed for The American Sportsman on ABC, although all did not go well at first as the salmon were not running. He did make up for it at the end of the week by catching a number of sea trout.