Herrera signed with the Pittsburgh Pirates as an international free agent in 2010. He received a $220,000 signing bonus. He then spent the next three years in the Pirates' farm system, advancing as far as the A-class West Virginia Power. Herrera, along with Gregory Polanco, represented the Pirates at the 2013 All-Star Futures Game. On August 27, 2013, the Pirates traded Herrera and a player to be named later, Vic Black, to the New York Mets to acquire Marlon Byrd and John Buck. His first season in the Mets organization was a success as he was promoted to Double A during the season.
New York Mets
2014
On August 28, after an injury to All-Star second baseman Daniel Murphy, Herrera was called up to the majors. He became the first Met player ever to start the season in single-A and get to the majors by the end of the season. Two days later, he collected his first major league hit off of the Phillies' Jerome Williams. He received his first RBI in the following game against Justin De Fratus. On September 1, Herrera hit his first Major League home run, off of Miami Marlins pitcher Henderson Álvarez. Herrera finished the season with appearing in 18 games with a batting average of.220 in 59 at-bats in 66 plate appearances while compiling 13 hits, 11 RBIs, 3 home runs, 7 walks, 6 runs scored and striking out 17 times.
2015
On May 1, Herrera was called up to the Mets as left-handed pitcher Jack Leathersich was sent down to the Las Vegas 51s. Herrera was called up to play second base with Daniel Murphy being moved to third base to stand-in for then-injured third basemenDavid Wright who was on the disabled list with spinal stenosis. Herrera was placed on the DL on May 15 due to a fractured tip of his middle finger. On June 11, he was reactivated off from the DL. On June 30, Herrera was sent down to the 51s to make room for Daniel Murphy who was coming off the DL. On September 7, he was recalled up due to the expanded rosters in September. Herrera finished the season appearing in 31 games with a batting average of.211 in 90 at-bats in 103 plate appearances while compiling 19 hits, 6 RBIs, 3 home runs, 11 walks, 7 runs scored, 2 stolen bases, and striking out 23 times. During the season on June 14, Herrera was seen wearing rally cups with the bottom of the cups cut out on his ears during the bottom half of the sixth inning. The Mets beat the Atlanta Braves 10-8 that day with Dilson going 1 for 3 with one hit, one RBI, one run scored and one walk. The one hit being a home run in the bottom of the 4th inning off Braves pitcher Mike Foltynewicz. It was well received by the members of the Mets and it drew a lot of positive media attention.
Cincinnati Reds
On August 1, 2016, the Mets traded Herrera and Max Wotell to the Cincinnati Reds in exchange for Jay Bruce. He was outrighted to AAA on March 13, 2018. On July 5, 2018, the Reds selected Herrera's contract from the Louisville Bats. He elected free agency on November 3, 2018.
Return to the Mets
On November 29, 2018, the Mets signed Herrera to a minor league contract, with an invite to Spring Training. On July 3, 2019, he opted out of his deal with the Mets and was released, making him a free agent. On July 5, 2019, he opted back into his minor league deal with the Mets, after having received offers from other minor league teams. On September 1, 2019, Herrera once again opted out of his minors deal, making him a free agent.
Baltimore Orioles
On December 5, 2019, Herrera signed a minor league contract with the Baltimore Orioles.
