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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.

On February 21, 2015, he signed a minor league contract with the Toronto Blue Jays. He elected free agency on November 6.

Dickerson signed a minor league contract with the Pittsburgh Pirates on January 6, 2014.

Dickerson was traded to the Cleveland Indians on July 7, 2014. He batted .224/.309/.327 for Cleveland. He was outrighted off the roster on September 9.

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.

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.

On March 25, 2011, Dickerson was traded to the New York Yankees in exchange for pitcher Sergio 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.

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.

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.

Dickerson was drafted again, in the 16th round (471st overall) 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.

A native of Hollywood, California, Dickerson attended Notre Dame High School. He was drafted out of high school by the New York Yankees in the 32nd round (968th overall) of the 2000 Major League Baseball Draft, but did not sign. He instead attended the University of Nevada, where he played college baseball for the Nevada Wolf Pack baseball team from 2001 through 2003. In 2002, he played collegiate summer baseball with the Brewster Whitecaps of the Cape Cod Baseball League.

Christopher Charles Dickerson (born April 10, 1982) is an American former professional baseball outfielder. Dickerson was drafted in the 16th round (471st overall) in 2003. He made his Major League debut in 2008. He played in Major League Baseball (MLB) for the Cincinnati Reds, Milwaukee Brewers, New York Yankees, Baltimore Orioles, and Cleveland Indians.