Freeland was drafted by the Philadelphia Phillies in the 35th round of the 2011 Major League Baseball draft, but did not sign and attended the University of Evansville. As a freshman in 2012, Freeland started 14 games, going 4–5 with a 4.55 earned run average and 70 strikeouts in 91 innings. As a sophomore in 2013, he again started 14 games, going 4–8 with a 4.34 ERA and 84 strikeouts in innings. After the season, he played in the Cape Cod League with the Hyannis Harbor Hawks, where he had a 2.25 ERA and 48 strikeouts. As a junior, he was 10–2 with a 1.90 ERA and 128 strikeouts over innings. Following his junior year, he was drafted by the Rockies.
Major League career
Considered a top prospect for the 2014 Major League Baseball draft, the Colorado Rockies selected Freeland in the first round, with the eighth overall pick, of the 2014 Major League Baseball Draft. Freeland spent 2014 with both the Grand Junction Rockies, and the Asheville Tourists, where he posted a combined 3-0 record with a 1.15 ERA between both teams. Freeland began the 2015 season with Grand Junction and was later promoted to the Modesto Nuts where he posted a 4.76 ERA. After the season, Freeland was assigned to the Salt River Rafters of the Arizona Fall League. In 2016, Freeland began the season with the Hartford Yard Goats, and was promoted to the Albuquerque Isotopes in June; Freeland posted an 11-10 record with a 3.89 ERA between the two clubs, starting 26 games. Freeland made his major league debut with the Rockies on April 7, 2017, against the Los Angeles Dodgers, and earned his first win. He also had his first major league hit, a single. His appearance marked the first time in 51 years that a starting pitcher made his Major League debut "in his team's home opener in the state in which he was born"; Chuck Dobson accomplished the feat for the Kansas City Athletics in 1966. Freeland hit his first and only home run on May 21, 2017 against Cincinnati Reds pitcher Bronson Arroyo. On July 9, Freeland took a no-hitter into the 9th inning against the Chicago White Sox before giving up a single to Melky Cabrera with one out. He finished the season with an 11-11 record in 156 innings. Freeland had a breakout season in 2018 and arguably the best season of any Rockies pitcher in franchise history. He finished the year by breaking Ubaldo Jimenez's franchise record for single season ERA at 2.84 and ended the year with a record of 17 wins and 7 losses in 33 starts. What made Freeland's record-breaking ERA more impressive is that he struggled badly in his first four starts, but went 17–4 with a 2.52 ERA in 29 starts the rest of the season. The native of Colorado also broke the single season franchise record for home ERA at one of the most notorious hitters parks in baseball in Coors Field, finishing with an outstanding ERA of 2.40. He pitched innings in 33 starts while striking out 173 batters against 70 walks and 182 hits, while holding opponents to a.240 batting average. Additionally, 24 of his 33 starts were quality starts, including 11 consecutive quality starts from August 6 to the end of the season. Freeland's extraordinary season, along with the stellar breakout season of strikeout artist and fellow ace German Marquez were widely credited with helping the Rockies reach the playoffs in consecutive years for the first time in franchise history. At the conclusion of the season, Freeland finished 4th in Cy Young voting Freeland went on to start the 2018 National League Wild Card Game. He pitched 6.2 shutout innings in which he struck out six while allowing only four hits and one walk as the Rockies defeated the Chicago Cubs 2-1 in 13 innings, the longest postseason elimination game in baseball history. Freeland also became the first Rockies pitcher to have a scoreless start in a postseason game. Freeland started the 2019 season horrendously, going 2-6 with a 7.13 ERA through 12 starts before being demoted to AAA on May 31. He was called back later in the month of June. Freeland ended with a 3-11 record in 22 starts.
