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.

Rollins began 2009 by participating in the 2009 World Baseball Classic (WBC) as a member of Team USA; he hit .417 and was named to the all-tournament team.
After setting a career high in stolen bases in 2008, he did not steal one in the season's first 17 games, his longest drought to begin a season since 2004.
On May 21, he reached the 1500-hit milestone in a game against the Cincinnati Reds.
As of the end of June, however, he was hitting just .205 (he went 28 consecutive at-bats without a hit from the end of June until July 2), and was benched for four games by Charlie Manuel in an effort to encourage him to regain the shorter, lower half-driven swing that he used in his 2007 MVP campaign.
He did improve in the second half of the season, batting .288 from July 3 to the end of the year.
Overall, he compiled an NL-leading 672 at-bats, finished fourth in doubles (43) and stolen bases (31), and tenth in runs (100); in addition, he had a .250 batting average, 21 home runs (five of which were leadoff, the most in his career), and 77 RBIs, also winning the National League Gold Glove award for shortstops.
In the postseason, he helped the Phillies reach the 2009 World Series by hitting a walk-off double in game four of the NLCS.
The Phillies failed to repeat as champions, however.
They lost to the New York Yankees.

Rollins's 2010 season was marked by injuries; he missed a total of 74 games, playing in only 88, the lowest total of his major league career.
While warming up in the outfield prior to the Phillies' game on April 12, he strained his right calf, and eventually was placed on the disabled list.
He spent April 13–May 16, and May 22–June 21 on the DL with that injury; Wilson Valdez served as his backup.
When he returned, he hit his first career walk-off home run on June 23, powering the Phillies to a 7–6 victory over the Cleveland Indians.
On July 3, he hit his 150th career home run in a game against the Pittsburgh Pirates, and on October 1, he hit his third career grand slam in a game against the Atlanta Braves.
Overall, he hit .243 with eight home runs and 41 RBIs.
He maintained his strong defense despite poor offense, but after his third consecutive mediocre offensive season, some questioned whether his MVP campaign in 2007 was a fluke.

2011 was a contract year for Rollins, and his performance concurrently rebounded, insofar as he improved his batting average, and home run and RBI totals.
He made his 11th consecutive opening day start, and, for the first time in several seasons, he was healthy at the beginning of the season, starting the season's first 49 games.
Nevertheless, it took him 54 plate appearances to record his first RBI, the longest drought of his career.
On July 20, for the second time in his career, he had a multi-home run game in which one home run came batting right
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.
Rollins began 2009 by participating in the 2009 World Baseball Classic (WBC) as a member of Team USA; he hit .417 and was named to the all-tournament team. After setting a career high in stolen bases in 2008, he did not steal one in the season's first 17 games, his longest drought to begin a season since 2004. On May 21, he reached the 1500-hit milestone in a game against the Cincinnati Reds. As of the end of June, however, he was hitting just .205 (he went 28 consecutive at-bats without a hit from the end of June until July 2), and was benched for four games by Charlie Manuel in an effort to encourage him to regain the shorter, lower half-driven swing that he used in his 2007 MVP campaign. He did improve in the second half of the season, batting .288 from July 3 to the end of the year. Overall, he compiled an NL-leading 672 at-bats, finished fourth in doubles (43) and stolen bases (31), and tenth in runs (100); in addition, he had a .250 batting average, 21 home runs (five of which were leadoff, the most in his career), and 77 RBIs, also winning the National League Gold Glove award for shortstops. In the postseason, he helped the Phillies reach the 2009 World Series by hitting a walk-off double in game four of the NLCS. The Phillies failed to repeat as champions, however. They lost to the New York Yankees.
Rollins's 2010 season was marked by injuries; he missed a total of 74 games, playing in only 88, the lowest total of his major league career. While warming up in the outfield prior to the Phillies' game on April 12, he strained his right calf, and eventually was placed on the disabled list. He spent April 13–May 16, and May 22–June 21 on the DL with that injury; Wilson Valdez served as his backup. When he returned, he hit his first career walk-off home run on June 23, powering the Phillies to a 7–6 victory over the Cleveland Indians. On July 3, he hit his 150th career home run in a game against the Pittsburgh Pirates, and on October 1, he hit his third career grand slam in a game against the Atlanta Braves. Overall, he hit .243 with eight home runs and 41 RBIs. He maintained his strong defense despite poor offense, but after his third consecutive mediocre offensive season, some questioned whether his MVP campaign in 2007 was a fluke.
2011 was a contract year for Rollins, and his performance concurrently rebounded, insofar as he improved his batting average, and home run and RBI totals. He made his 11th consecutive opening day start, and, for the first time in several seasons, he was healthy at the beginning of the season, starting the season's first 49 games. Nevertheless, it took him 54 plate appearances to record his first RBI, the longest drought of his career. On July 20, for the second time in his career, he had a multi-home run game in which one home run came batting right
Jimmy Rollins