Cliff Swain was born on March 21, 1966 in San Jose, California and was raised in Braintree, Massachusetts. Swain was introduced to racquetball by his father, Robert "Red" Swain, a competitive handball player when Cliff was 13 years old . Swain was a naturally talented and quickly picked up the game, soon winning Massachusetts State and New England Regional Junior Racquetball Championships. In 1983 Cliff Swain won the US Junior National 16 and Under Racquetball Championship. In 1984 Swain won the Orange Bowl World 18 and Under Junior Racquetball Championship. Swain played on the racquetball team at Providence College in 1984 before turning professional.
Swain's 71 IRT tournament wins is more than any other IRT player (Marty Hogan is second with 60), and he has also played more tournaments 265 than any other player (second is Ruben Gonzalez at 200). Swain's career highlights are his two US Open Racquetball Championships in 1997 and 2001. Swain was the season end #1 IRT player 6 times: 1990, 1993-95, 1998 and 2002.
Swain won his first professional racquetball title in 1985 at the Tulsa Open in Tulsa, Oklahoma. Swain went on to win the 1985 Ektelon National Championship in his first season on tour, consecutively beating racquetball legends, Marty Hogan, Dave Peck and Greg Peck. Swain was named the Professional Racquetball Rookie of the Year in 1985. Cliff remained one of the top ten professional players from 1985 to 1989. In 1990 Swain finished the year as the number one ranked player in the world for the first time. Swain would go on to finish number one five more times in 1993, 1994, 1995, 1998 and 2002. Swain won over eighty tournaments in his pro career including the 1997 and 2001 US Open Racquetball Championships.
In 2003, Swain was inducted in to the USA Racquetball Hall of Fame. In 2004 and 2005 Cliff played the Legends Racquetball Tour winning the Legends 35+ National Championship both years. Cliff Swain teamed with fellow racquetball legend, Marty Hogan to win the 2004 and 2005 Legends National Doubles Championships. In 2008 Cliff Swain teamed with Woody Clouse to win the 40+ USA Racquetball National Doubles Championship.
Swain would likely have won more racquetball tournaments, but in 1990 at the age of 24, he left racquetball to pursue a tennis career at the encouragement of Ion Tiriac, one time coach of Boris Becker. That pursuit lasted two years and although Swain had some success, it was not nearly at the level he had experienced in racquetball.