Midre Cummings, a native of the U.S. Virgin Islands, embarked on his Major League Baseball journey when he was drafted by the Minnesota Twins in the first round of the 1990 MLB Draft. His professional debut came with the Pittsburgh Pirates, where he played as an outfielder. Cummings' time with the Pirates marked the beginning of his MLB career, showcasing his potential as a reliable player in the outfield.

Throughout his career, Cummings played for several teams, including the Philadelphia Phillies, Boston Red Sox, Minnesota Twins, Arizona Diamondbacks, Tampa Bay Devil Rays, and Baltimore Orioles. His role often involved being a utility outfielder, providing depth and flexibility to the teams he joined. Cummings was known for his speed and defensive skills, which made him a valuable asset in various outfield positions.

In 1997, Cummings joined the Philadelphia Phillies, where he continued to develop his skills. His tenure with the Phillies was followed by a brief stint with the Boston Red Sox in 1998. The following year, he returned to the Minnesota Twins, the team that initially drafted him. During his time with the Twins, Cummings contributed both offensively and defensively, adding depth to their roster.

Cummings' journey continued with the Arizona Diamondbacks in 2000. Although his time with the Diamondbacks was short, he was part of a team that would go on to win the World Series the following year. In 2001, he signed with the Tampa Bay Devil Rays, where he spent two seasons. His experience and versatility were valuable to the Devil Rays as they navigated the challenges of building a competitive team.

In 2003, Cummings joined the Baltimore Orioles, marking the final chapter of his MLB career. His experience and leadership were assets to the Orioles, providing guidance to younger players on the team. After his time with the Orioles, Cummings continued to play in minor league baseball, further extending his career in the sport he loved.

Throughout his MLB career, Midre Cummings played in over 400 games, demonstrating his ability to adapt and contribute to various teams.