Ross played college baseball for Auburn University and the University of Florida and participated in two College World Series. He started his major league career playing for the Los Angeles Dodgers in 2002 and also played for the Pittsburgh Pirates, San Diego Padres, Cincinnati Reds, Boston Red Sox, Atlanta Braves, and Chicago Cubs. Ross had two World Series wins with the Boston Red Sox in 2013 and the Chicago Cubs in 2016. The Cubs named him their manager prior to the 2020 season.