Unlike in spring training 2007, Rollins "made no guarantees heading into the next season, but that didn't mean the Phillies weren't confident" entering their 2008 season, despite the Mets' acquisition of Johan Santana and a "2007 Rollins-esque" guarantee of winning the division from Carlos Beltrán. After beginning the season by hitting a home run on opening day, Rollins landed on the disabled list (DL) for the first time in his career in early April, suffering an ankle sprain. He returned in May, and had a "productive" summer, ultimately posting a career-high 47 stolen bases, notwithstanding his batting average dropping to .277, and his home run and RBI totals dropping to 11 and 59 respectively. In the postseason, Rollins was a focal point of the team, which ultimately won the 2008 World Series; in the division series (NLDS), he hit a leadoff home run in game four, and in the championship series (NLCS), he hit a leadoff home run in game five, and despite struggles early in the World Series, he eventually contributed with strong situational hitting, helping the Phillies win the series in five games. At the conclusion of the season, Rollins was honored with a Fielding Bible Award for defensive excellence as the top MLB shortstop during the year.