Dickerson began the 2014 season with the Rockies, but was optioned to the Colorado Springs Sky Sox of the Class AAA Pacific Coast League on April 9 when Boone Logan was activated from the disabled list. On June 18, 2014, in a game versus the Los Angeles Dodgers, Dickerson was the only batter to reach base safely during Clayton Kershaw's no-hitter, reaching on an error. In 2014 in the majors he batted .312(9th-best in the league)/.364/.567(3rd-highest in the NL) with 24 home runs, 18.2 at-bats-per-home-run (6th-best in the NL), and 76 RBIs in 436 at bats.
Dickerson and his wife, Beth Anne, had a son, Davis, in 2014. On February 22, 2018, the same day he was traded to the Pirates, the couple had their second son, Miller. In the offseason, Dickerson resides in Madison, Mississippi.