In 2007, he was named the Philadelphia Daily News' Player of the Year as a high school senior.

As a senior, he was named an honorable mention NCAA Men's Basketball All-American, by the Associated Press.

For the 2012–13 season, Wanamaker moved to Limoges of France's top league, the LNB Pro A, where he averaged 9.0 points and 3.4 rebounds per game.

[3] The following season, Wanamaker returned to Italy and signed with Giorgio Tesi Pistoia of Lega Basket Serie A.

In the German BBL, Wanamaker was named the Most Valuable Player,[8] after leading the Bamberg team to a second straight national domestic league championship.

[13] Wanamaker made his NBA debut on October 16, recording 2 points and 1 rebound in a blowout 105–87 win over the Philadelphia 76ers.

On November 24, 2020, Wanamaker signed with the Golden State Warriors[16] as a free agent to play backup point guard behind Stephen Curry.