Small turned professional in 1990 and played on various tours before joining the PGA Tour in 1995. In 1997, he won two Nike Tour events and finished in the top 15 on the Nike Tour money list, earning his PGA Tour card for the 1998 season. He played on the PGA Tour in 1998, where his best finish was 9th place at the Bell Canadian Open. In 2003, Small won the Illinois PGA and Illinois Open titles, becoming the first golfer ever to win both tournaments in the same year. He would repeat that feat three more times on the way to winning twelve IPGA titles and four Illinois Opens. He has played in 96 Nationwide Tour events finishing in the top-10 eight times. Small has also won the PGA Professional National Championship thrice, in 2005, in 2009, and in 2010. He has played in over 50 PGA Tour events in his career, including twelve major championships. In 2016, he turned 50 and qualified for his first senior major championship, finishing T-43 at the U.S. Senior Open. He has also finished as the low club professional in the PGA Championship in 2007 and 2011. Small has been the head golf coach at the University of Illinois since 2000. He was Big Ten Coach of the Year for the 2001-02 season, when Illinois placed 18th in the NCAA Championships. He won the honor again for the 2008-09 season when Illinois won their first Big Ten title in 21 years. He led the Illini to the Big Ten championship in each of the next four seasons, again winning conference coach of the year honors each year. In addition, he has been named Midwest Coach of the Year by the Golf Coaches Association five times, in 2003, 2009, 2010, 2011 and 2013. His 2013 Illini team won the school's first-ever NCAA Regional championship, and finished second in the NCAA Finals after defeating defending champion Texas and #1-ranked California in match play. It marks Illinois' best finish in school history. On October 25, 2013, Small was inducted into the Illinois Golf Hall of Fame.
Personal life
Small's father, Bill Small, was captain of the 1963 Big Ten Champion Illinois Fighting Illini men's basketball team and earned All Big-Ten honors. Small's brother, Andy, was a member of the 1990 Big Ten Champion Illinois baseball squad and won four varsity letters as an infielder.
Amateur wins (3)
1984 Junior Masters
1987 Butler National Intercollegiate, Michigan State Spartan Classic