Dickerson was drafted by the Pittsburgh Pirates in the third round of the 2011 Major League Baseball draft. After signing for a signing bonus of $380,700, Dickerson spent most of the rest of the 2011 season with the State College Spikes, batting.313/.393/.493 with an.886 OPS in 150 at bats; his 16 doubles were second among all short-season batters. Dickerson spent the 2012 season with the Bradenton Marauders, where he batted.295/.353/.451 with 31 doubles, 13 home runs, and 90 RBIs in 488 at bats and was named the Florida State League Player of the Year, a post-season All Star, and an MiLB organization All Star. Prior to the 2013 season, Dickerson was named the 7th-best first base prospect in baseball by MLB.com. He spent 2013 with the Double-A Altoona Curve, where he moved from first base to the outfield. He batted.288/.337/.494 with 36 doubles, 17 home runs, and 68 RBIs in 451 at bats and was named the Eastern LeagueRookie of the Year, a post-season All Star, and an MiLB organization All Star.
On November 25, 2013, Dickerson was traded to the San Diego Padres for Jaff Decker and Miles Mikolas. Dickerson severely sprained his left ankle in 2014 spring training with the Padres when he stepped on a sprinkler head, and an MRI later found a bone cyst in his left heel which required surgery and a bone graft. The surgery delayed his start to the 2014 season, but he finished with 34 games with the Double-A San Antonio Missions, batting.321/.367/.496 in 137 at bats. On November 20, 2014, the Padres added Dickerson to their 40-man roster to protect him from the Rule 5 draft. Dickerson spent most of 2015 with the Triple-AEl Paso Chihuahuas, hitting.307 /.374/.503 with 82 runs, 36 doubles, 9 triples, 12 home runs, and 71 RBIs in 459 at bats over 125 games, including 88 starts in left field. His performance earned him the Pacific Coast League Rookie of the Year Award, and he was named a post-season All Star and an MiLB organization All Star. On August 6, 2015, Dickerson made his Major League debut with the San Diego Padres with a pinch-hitting appearance in the 8th inning. He was called up to replace Will Venable, who went on paternity leave. The next day, Dickerson collected his first Major League hit with a pinch single in extra innings. Dickerson returned to the Padres when rosters expanded in September. A tweaked hip flexor limited his playing opportunities, but Dickerson appeared in eight more games as a pinch hitter, and once as a defensive substitute in left field. Dickerson started the 2016 season in Triple-A El Paso. On May 2, the Padres recalled Dickerson from Triple-A. On May 10 against the Chicago Cubs at Wrigley Field, Dickerson hit a pinch-hit grand slam off of Adam Warren for his first career home run and his first four career RBIs. He made his first Major League start in left field the following day, but was returned to El Paso on May 14. With the Chihuahuas, he continued a 28-game minor league hitting streak through the end of May. On June 28, Dickerson was recalled from El Paso when Jon Jay broke his forearm. Dickerson remained as the regular left fielder for the Padres for the remainder of the season. For the season, with El Paso he batted.382/.425/.622 with 10 home runs and 51 RBIs in 217 at bats. He finished the season with the Padres with a.257/.333/.455 batting line and 39 runs, 10 home runs, and 37 RBIs in 285 plate appearances. He made 65 starts in left field. In spring training of 2017, Dickerson suffered a bulging disk. After initially trying to rehab the injury, Dickerson underwent back surgery by microdiscectomy to remove bulging disc material in his lower back which ended his season. In spring training of 2018, while trying to come back from his back surgery, Dickerson tore his UCL in his elbow and underwent Tommy John surgery, costing him another full season. He was outrighted off the roster after the season. He elected free agency on November 3, 2018, and later re-signed to a minor league deal on December 11. Playing for AAA El Paso in 2019, he hit.372/.469/.606 with 5 home runs and 20 RBIs in 94 at bats. Dickerson had his contract selected to the major leagues on May 3, 2019, but after 19 at bats with the Padres was designated for assignment on June 5.
San Francisco Giants
On June 10, 2019, Dickerson was traded to the San Francisco Giants in exchange for Franklin Van Gurp. He played seven games for AAA Sacramento. On June 21, in his first game with the Giants, he hit a grand slam and had a career-high 6 runs batted in. With the Giants in 2019, he batted.290/.351/.529 with 28 runs, 6 home runs, and 26 RBIs in 155 at bats.
