While at Proctor, Dyson matured and was recruited to play basketball with the University of Connecticut Huskies under coach Jim Calhoun.

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.

[3] Dyson went undrafted in the 2010 NBA draft and played with the Cleveland Cavaliers and Oklahoma City Thunder during the 2010 summer league and preseason before being cut.

[4][5] Following the season, Dyson was named to the United States men's national basketball team for the 2011 Pan American Games in Guadalajara, Mexico.

The team, composed entirely of non-NBA players due to the 2011 NBA lockout, finished with the bronze medal.

[16] During that season, Dyson won Israeli League Cup with Jerusalem, as well as reaching the EuroCup semifinals.

[19] On December 16, 2017, Dyson recorded 29 points, 3 rebounds and 3 assists, including a game-winning layup with 10.9 seconds left in an 88–86 win over Hapoel Holon.

[20] On January 15, 2018, Dyson recorded a season-high 30 points, shooting 8-for-11 from the three-point range, along with 5 assists and 3 steals, in a 92–78 win over Maccabi Rishon LeZion.

[21] During his second season with Jerusalem, Dyson participated in the Israeli League All-Star Game and the Three-Point Shootout during the same event.

[26] Dyson led Jerusalem to the 2018 Israeli League Final Four, where they eventually lost to Hapoel Holon.

[30] On February 26 he transferred to Fortitudo Bologna[31] that was looking for someone to replace Kassius Robertson who was injured with the Canadian national team during the 2021 FIBA AmeriCup qualifiers.