Roberts first made his debut in Baltimore in 2001, and by 2003, he was the team’s starting Second Baseman. He would be chosen for the All-Star Team in both 2005 and 2007, and in 2004 and 2009, he was the American League leader in Doubles. From 2003 to 2009, Roberts would have at least 23 Stolen Bases, and he peaked in that category in 2007 with 50. That number would also lead the league. His play drastically declined in 2010 with back trouble, and he also was plagued with many more injuries over the next few seasons. He would leave the O's when he signed with the New York Yankees in 2014.With Baltimore, Roberts would bat .278 with 1,452 Hits and 278 Stolen Bases.