Derek Holland, a left-handed pitcher, began his Major League Baseball career with the Texas Rangers. Drafted in the 25th round of the 2006 MLB Draft, Holland quickly rose through the minor league ranks, making his MLB debut with the Rangers in 2009. Known for his fastball and slider, he became a reliable starter for the team.

Holland's early years with the Rangers were marked by both promise and challenges. In 2010, he played a role in helping the Rangers reach the World Series, although they ultimately fell to the San Francisco Giants. The following year, Holland delivered one of his most memorable performances in Game 4 of the 2011 World Series against the St. Louis Cardinals. Pitching 8 1/3 innings, he allowed only two hits and no runs, helping the Rangers secure a crucial victory. Despite his efforts, the Rangers lost the series in seven games.

Injuries, however, began to affect Holland's career. He faced several setbacks, including a knee injury in 2014 that required surgery and limited his playing time. Despite these challenges, he continued to contribute to the Rangers' pitching rotation when healthy. By the end of his tenure with Texas in 2016, Holland had accumulated a record of 62 wins and 50 losses with an ERA of 4.35.

Following his time with the Rangers, Holland signed with the Chicago White Sox for the 2017 season. His stint with the White Sox was short-lived, as he struggled to find consistency on the mound, finishing the season with a 7-14 record and a 6.20 ERA. The White Sox released him in September 2017.

Holland's career took a positive turn when he joined the San Francisco Giants in 2018. He enjoyed a resurgence, posting a 3.57 ERA over 171.1 innings and becoming a valuable member of the Giants' pitching staff. His performance earned him a one-year contract extension with the team for the 2019 season. However, his second year with the Giants was less successful, leading to his release in July 2019.

The Chicago Cubs picked up Holland shortly after his release from the Giants, and he finished the 2019 season with them, primarily working out of the bullpen. In 2020, Holland signed a minor league deal with the Pittsburgh Pirates and made the team's Opening Day roster. During the pandemic-shortened season, he appeared in 12 games, starting five, and recorded a 6.86 ERA.

In 2021, Holland signed a minor league contract with the Detroit Tigers. He made the team's roster and appeared in 39 games, mostly as a reliever. Despite his efforts, he struggled with consistency, finishing the season with a 5.07 ERA.