Ranking Derek Jeter's Top 5 Yankees vs. Red Sox Rivalry Moments

Derek Jeter enjoyed one more signature moment in his storied career on Thursday night, hitting a walk-off single in his last at-bat at Yankees Stadium.

It was a fitting end to Jeter’s time in New York. The shortstop has served as the face of the Yankees and one of the faces of baseball since 1995. His absence next season will be strange for all.

The Boston Red Sox and their fans, of course, have a complicated relationship with Jeter. On the one hand, he served as the captain of “the evil empire” for more than a decade, and his timely hits and flashy shortstop play caused much pain and suffering around New England for many a year.

On the other hand, Jeter has been a part of baseball for as long as many younger fans can remember, and with Jeter and Mariano Rivera missing from Red Sox-Yankees games, they just won’t feel the same.

But whether Red Sox fans loved to hate Jeter or hated to admit that some part of them loved him, there’s no doubting the impact he had on the rivalry for many, many years. With his final stint against the Red Sox kicking off on Friday night, let’s take a look at five of Jeter’s most memorable moments against his chief rivals.

5. 1999 All-Star Game, Fenway Park

The 1999 All-Star Game at Fenway Park was one of the more memorable in recent history not because of anything that happened during the course of play—the AL beat the NL 4-1—but because Ted Williams was in attendance.

The reaction from the players on the field was incredible, as all of the game’s modern stars flocked to Williams’ spot on the field to speak to the legendary slugger.

MATT YORK/Associated Press

Jeter, of course, was in attendance, as a reserve in what would become one of his 14 All-Star Game experiences. Red Sox star Nomar Garciaparra earned the starting nod over Jeter, back when the “Jeter vs. Nomar” debate was at its peak.  

Jeter went 0-1 in his lone at-bat, but that doesn’t matter. It’s appropriate that he was a part of one of Fenway’s most meaningful moments of the last several decades, and when we look back on Williams’ reception in another 10 or 20 years, we’ll be amazed that other all-time greats like Jeter, Ken Griffey Jr., Cal Ripken, Pedro Martinez, Randy Johnson and Barry Larkin were all on the field at the same time.

4. April 5, 2005

After their dramatic and wildly entertaining ALCS matchup in 2004, the Red Sox and Yankees opened up the 2005 season playing against each other in New York. The first game on April 4 was a 9-2 route for the Yankees, uncharacteristic of how closely these two teams were matched.

But the second on April 5 was a different story and saw the Red Sox and Yankees fight down to the bitter end. The Red Sox entered the top of the ninth down by a run, and with Mariano Rivera on the mound, that generally meant the game would be over soon.

Then Jason Varitek took Rivera deep to tie the game at 3-3, and it looked like Rivera’s postseason demons would haunt him once again.

Jeter, however, had other plans. With Keith Foulke on the mound for the Red Sox in the bottom of the ninth, Jeter led off the inning with a solo homer over the right field fence, giving the Yankees the victory.

For Red Sox fans who planned to enjoy their recent conquest over the Yankees, Jeter’s victory was an unwelcome reminder of Yankee-dominated years in the recent past.

3. Jeter’s First MLB Walk-Off Hit

In retrospect, it’s quite fitting that Jeter’s first-ever walk-off hit came against the Red Sox.

On September 21, 1996, the Red Sox and Yankees found themselves tied at 11 in the bottom of the 10th inning. Jeter hit a seeing-eye single off Joe Hudson just past Garciaparra with two outs and the bases loaded. Wade Boggs came home to score, and Yankees fans went home happy.

It was the first but certainly not the last time Jeter ended a major league game with his bat, and the hit extended the Yankees’ lead in the AL East to five games over the Baltimore Orioles.

While Jeter had received a cup of coffee in the majors in 1995, 1996 was his rookie season, and he was just starting to earn a name for himself as one of the game’s best young players. Jeter would go on to win the 1996 AL Rookie of the Year award, and the Yankees would go on to win the 1996 World Series.

2. 2003 ALCS, Game 3

Harken back, if you will, to the 2013 postseason. The Red Sox-Yankees rivalry was in its halcyon days, with the Sox still mired in their 86-year World Series drought and the Yankees still fresh off their dominant five-year run.

Game 3 of the ALCS marked a pivotal moment in the series as Pedro Martinez and Roger Clemens squared off with the series tied 1-1. As we know now, it would prove to be one of the wildest postseason games of the decade, with Martinez shoving down Don Zimmer, Clemens throwing at Manny Ramirez and Jeff Nelson getting into a scuffle with a member of the Fenway grounds crew.

It’s against that backdrop that Jeter helped to break the hearts of many Red Sox fans, taking Martinez deep in the top of the third with a solo home run. Eventually, the Yankees would go on to win the game and the series, with Aaron Boone’s towering home run in Game 7 off Tim Wakefield a lasting memory for Sox and Yankees fans alike.

In many ways, it was that series that brought the rivalry to new heights. The Yankees went out and traded for Alex Rodriguez in the offseason, while the Red Sox imported Curt Schilling. And as we all know, the Sox would eventually defeat their demons in 2004 with the greatest comeback in MLB postseason history.

But back in 2003, it felt as though the Red Sox would never surpass the Yankees, and Jeter was a big part of the reason why.

1. The Dive, 2004

For many Red Sox fans, there’s no more memorable Jeter play than “The Dive.”

On July 1, 2004, the Yankees and Red Sox were tied 4-4 in the bottom of the 12th inning, and with runners on second and third, Trot Nixon stepped to the plate. Nixon fought a pitch off along the third base line for what many assumed—and what usually is—a foul ball out of reach of the field of play.

Jeter tracked the ball regardless, and made one of the most incredible catches of his career, vaulting three rows deep into Yankee Stadium's stands. Sacrificing his body, the shortstop emerged from a pile of spectators, bloodied, bruised...and somehow with the ball secure in his glove.

Jeter would have to leave the game, but the Yankees would eventually go on to win the contest and sweep the Red Sox, right when the rivalry was at its peak.

Perhaps Jeter’s postseason flip against the Oakland Athletics is his most famous single play ever, and his twist-and-throw motion from shortstop is his signature move. But for many Boston fans, there’s no more famous Jeter moment than The Dive, and the contrast between Jeter’s efforts and Garciaparra sitting out that game was stark.

It’s tough to choose just one Jeter vs. Red Sox moment to rank above them all, but The Dive was a great enough play to deserve such an honor.