He played college basketball for Villanova before being selected with the 33rd overall pick in the 2009 NBA draft by the Portland Trail Blazers.

[1] As a senior, Cunningham transferred to Potomac High School, which he led to a 27–0 season under Head Coach Rico Reed.

[1] In his senior year, Cunningham would go on to lead the team in scoring with 16.1 points and take home the Big East Most Improved Player award.

He played for Portland's Las Vegas Summer League team where he averaged over 18 points and 5 rebounds per game in four contests.

[2] On February 24, 2011, Cunningham was traded, along with Joel Przybilla, Sean Marks and two future first-round draft picks, to the Charlotte Bobcats in exchange for Gerald Wallace.

[13] On July 7, 2021, Cunningham signed with the Cangrejeros de Santurce of the Baloncesto Superior Nacional.

[18] However, he was later ruled ineligible to compete for Britain after an investigation by British Basketball officials into his ancestral ties failed to prove his case to receive UK citizenship.