Todd Hollandsworth embarked on his Major League Baseball journey when he was drafted by the Los Angeles Dodgers in the third round of the 1991 MLB Draft. His debut in the major leagues came on April 25, 1995, with the Dodgers. Known for his outfield capabilities, Hollandsworth quickly made a name for himself in his rookie season. In 1996, he earned the National League Rookie of the Year award, becoming the fifth consecutive Dodger to win the honor, following in the footsteps of Eric Karros, Mike Piazza, Raul Mondesi, and Hideo Nomo.

During his time with the Dodgers, Hollandsworth was recognized for his batting skills and speed on the field. However, injuries began to affect his playing time and performance. Despite these challenges, he remained a valuable player for the Dodgers until he was traded to the Colorado Rockies in 2000. His tenure with the Rockies was marked by a solid performance, but he was again hampered by injuries that limited his time on the field.

In 2002, Hollandsworth signed with the Texas Rangers, where he played for a brief period before being traded to the Florida Marlins. His stint with the Marlins proved to be a highlight in his career. In 2003, he played a role in the Marlins' journey to winning the World Series, although injuries limited his participation in the postseason. Nonetheless, he contributed during the regular season and was part of the team that clinched the championship.

Following his time with the Marlins, Hollandsworth continued his career with several other teams. He joined the Chicago Cubs in 2004, where he served as a valuable bench player and occasional starter. His performance with the Cubs was marked by a strong batting average and the ability to deliver in clutch situations. However, injuries once again curtailed his playing time.

Hollandsworth's career also included brief periods with the Atlanta Braves and Cleveland Indians. With the Braves, he played in the 2005 season, and in 2006, he joined the Indians, where he concluded his major league career. Throughout his time in MLB, Hollandsworth was known for his left-handed batting and outfield versatility, often being utilized as a pinch hitter or platoon player.