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.[3] Swain was 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.