A small forward, he played college basketball for the Boston Terriers and represents the Puerto Rican national team.

Holland attended Fordham Prep where he averaged 16 points, eight rebounds, eight assists and three steals, earning a McDonald's All-American nomination, a CHSAA All-Division naming and All-County honors from the Journal News.

He also played for Saint Benedict's Prep where he averaged 10 points, six rebounds, six assists, three steals and two blocks per game.

[1] Holland played college basketball for Boston University where as a junior in 2009–10, he led the America East Conference in scoring with 19.2 points per game.

He was subsequently named America East Conference Men's Basketball Player of the Year and led the Terriers to an NCAA Tournament berth.

[10] He made his debut for the Charge later that night against the Grand Rapids Drive, recording 11 points, 3 rebounds, 5 assists and 2 steals in a 113–111 loss.

[12] On April 19, he made his debut for the Celtics in an 89–72 playoff loss to the Atlanta Hawks, playing one minute off the bench.

[20] On November 19, 2018, the Austin Spurs announced that they had acquired the returning right to Holland and a 2019 second-round pick from the Canton Charge in exchange for Jaron Blossomgame.

On December 26, 2019, Holland signed with Hapoel Jerusalem of the Israeli Basketball Premier League as a replacement for Trent Lockett.

[24] On July 27, 2020, Holland signed with Russian club UNICS Kazan of the VTB United League.

He first represented the Puerto Rican national team in 2011 when he played in the 2011 Jenaro Marchand Continental Championship Cup.