2003 proved to be a very successful year for Singh. He won four tournaments, had 18 top-10 finishes and was the PGA Tour's money leader (and had the second highest single-season total in PGA Tour history) with $7,573,907, beating Tiger Woods by $900,494, though Singh played 27 tournaments compared to Woods' 18 tournaments. Singh also tied a 9-hole scoring record at the U.S. Open with a 29 on the back nine of his second round. His victories came at the Phoenix Open, the EDS Byron Nelson Championship, the John Deere Classic and the FUNAI Classic at the Walt Disney World Resort. He narrowly lost the vote for the PGA of America's Player of the Year to Tiger Woods.
However, the 2003 season was also spotted with controversy involving Singh surrounding the year's event at the Bank of America Colonial. LPGA star Annika Sörenstam became the first woman to play at a PGA Tour event since Babe Zaharias at the 1945 Los Angeles Open. Surrounding this fervor, Singh was misquoted as having said that Sörenstam "didn't belong" on the men's tour and that he would not play if he were paired with her. What he actually said is that he would not be paired with her because his playing partner was being selected from the past champion's pool. Singh later clarified, "There are guys out there trying to make a living. It's not a ladies' tour. If she wants to play, she should—or any other woman for that matter—if they want to play the man's tour, they should qualify and play like everybody else."
Controversy surrounded Singh in 2003 before the Bank of America Colonial. Annika Sörenstam was scheduled to play the event, and Singh was quoted as saying, "I hope she misses the cut ... because she doesn't belong out here." He later said that the substance of his interview to an Associated Press reporter was that she would be displacing some other struggling male player, for whom he had his sympathies. However, the media focused on this statement. Golf Digest wrote that Singh had become "pro golf's bad guy".