[2] Dickens was signed as a free agent by the Portland Trail Blazers on December 19, 2003, and appeared in 3 games for them during the 2003–04 season.

In 29 games (28 starts), prior to his NBA callup, Dickens averaged a team high 20.4 points and 5.2 rebounds.

On February 22, 2008, Dickens was signed to a ten-day contract with the Cleveland Cavaliers so they would have enough players to face the Washington Wizards that night, due to a depleted roster because of a blockbuster trade the day prior.

[3][4] Dickens saw his first action as a Cavalier on that very night, logging seven minutes with one rebound and a blocked shot.

Dicken's final NBA game was played on March 6, 2008, in a 96 - 107 loss to the Chicago Bulls.