From 2006 to 2008 he played for the Cincinnati Reds. Ross played for the Boston Red Sox in 2008 and the Atlanta Braves from 2009 to 2012. From 2013 to 2014 he played for the Boston Red Sox and he finished his career playing for the Chicago Cubs from 2015 to 2016. Ross won two World Series championships. His first was with the Red Sox in 2013 and his second came with the Cubs in 2016. In 2017 he became the first baseball player to compete on the reality television series Dancing with the Stars.