Dickerson was drafted again, in the 16th round of the 2003 MLB Draft, this time by the Cincinnati Reds. He made his Major League debut with the Reds on August 12, 2008. He hit his first career home run on August 15, 2008, against the St. Louis Cardinals. Dickerson earned a starting job in the outfield with Jay Bruce and Willy Taveras entering the 2009 season, due to Ken Griffey and Adam Dunn's departures. In the first month of the season, Dickerson was only batting.205 with a homer and 5 RBIs. However, by the end of May he boosted his average to.271. He also was featured in highlight reels for his defensive plays while filling in for Tavares at center field. In 2010 he batted.205 for Cincinnati.
Milwaukee Brewers
On August 9, 2010, Dickerson was traded to the Milwaukee Brewers for outfielder Jim Edmonds. Dickerson batted.208 with 5 RBIs in 25 games with Milwaukee.
New York Yankees
On March 25, 2011, Dickerson was traded to the New York Yankees in exchange for pitcherSergio Mitre. He made his Yankees debut on May 17, going 1-for-3 with one run batted in. He was promoted again to the Major Leagues in September. Dickerson cleared waivers before the 2012 season and was outrighted to the Class-AAA Scranton/Wilkes-Barre Yankees. Dickerson was promoted to the Major Leagues again on September 1, after the rosters expanded. The Yankees designated Dickerson for assignment, and subsequently released him in January 2013.
Baltimore Orioles
Dickerson signed a minor league contract with the Baltimore Orioles for 2013 and was assigned to the AAA Norfolk Tides. He was called up to Baltimore on April 10, and made his Orioles debut that night. On May 21, Dickerson hit two home runs off Phil Hughes for his first career multi-homer game. On May 31, Dickerson hit the first walk-off home run of his career against Detroit Tigers pitcher José Valverde. Dickerson was designated for assignment on July 19. He batted.238 for Baltimore. After clearing waivers, he was outrighted to the minors. He refused the assignment and became a free agent.
On February 21, 2015, he signed a minor league contract with the Toronto Blue Jays. He elected free agency on November 6.
Return to Baltimore
On August 29, 2016, Dickerson signed a minor league deal with the Orioles. He signed another minor league contract with the Orioles on December 16. He elected free agency on November 6, 2017.
Community
Along with fellow baseball player Jack Cassel, Dickerson is a founder of Players for the Planet, a foundation that brings professional athletes together to inspire communities to build awareness of the growing environmental crisis. Several athletes including Chase Utley, Jay Bruce, Ryan Braun, Matt Cassel, and Jacoby Ellsbury are on board to spread the awareness.