In his junior season at San Leandro High School, Cunningham averaged 17.8 points, 4.5 rebounds and 3.3 assists per game.

[2] In Cunningham's freshman season at Oregon State, he averaged 6.2 points, 2.0 rebounds, and 0.9 assists per game.

In a first-round game against Boston University in the 2010 College Basketball Invitational, he recorded a then career-high of 21 points.

He was also named to the Pac-10 All-Tournament Team after averaging 23.5 points per game in the 2011 Pacific-10 Conference men's basketball tournament.

[13] In July 2014, he joined the Kings for the 2014 NBA Summer League but did not receive a new contract offer from the team.

[20] On February 18, 2016, he was traded, along with a future second-round pick, to the Orlando Magic in exchange for Channing Frye.

[23] The next day, he made his season debut for Idaho in a 114–113 loss to the Texas Legends, recording 30 points and three rebounds in 26 minutes.

[25] On March 20, he made his debut for the Bucks in a 94–85 loss to the Utah Jazz, recording four points, one rebound, one assist and one steal in 16 minutes off the bench.

[30] On August 29, 2017, Cunningham signed a one-year deal with Bayern Munich of the German Basketball Bundesliga (BBL) and the EuroCup.

On November 28, 2018, Cunningham signed a deal with Italian basketball club Basket Brescia Leonessa of the LBA.

[38] On December 14, 2022, Cunningham signed with Pieno žvaigždės Pasvalys of the Lithuanian Basketball League (LKL).