Dyson grew up in Potomac, Maryland's Scotland neighborhood. He attended Winston Churchill High School in Potomac for his first two years of high school before transferring to Proctor Academy in Andover, New Hampshire for his final two years. While at Proctor, Dyson matured and was recruited to play basketball with the University of Connecticut Huskies under coach Jim Calhoun. During his freshman season at UConn, Dyson was compared by Calhoun to NBA players and UConn alumni Ray Allen and Richard Hamilton. During his sophomore season, he and teammate Doug Wiggins were caught by on-campus police in a car with alcohol and a small amount of marijuana. He was eventually reinstated. In February 2009 during his junior year, he tore a lateral meniscus in his right knee in an on-court collision with Syracuse University guard Andy Rautins. At the time of the injury, he had started all 24 games for the Huskies, scoring in double figures 18 times and averaging 13.2 points per game. He returned the following season and scored 17.7 points and 4.4 assists per game. In March 2010, the Sporting News named Dyson their 2010 Comeback Player of the Year.

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