6 Most Entertaining Moments in Yankees-Red Sox Rivalry

A fierce rivalry many would label the best in sports has produced countless classics over the past century. From Bucky's blast to a bloody sock, the Yankees and Red Sox have epitomized baseball as America's pastime. 

The bad blood dates all the way back to 1903 when the New York Highlanders faced off against the Boston Americans for the very first time at Huntington Avenue Grounds. 

Now, 109 years later, the two teams have battled on more than 2,100 occasions. 

It never gets old. 

When the Yankees and Red Sox are playing, every statistic and measurement is thrown out the window. Records are dismissed and pitching matchups ignored. 

Because when these two teams take the diamond, anything can happen. 

Just ask David Ortiz. 

With Boston's underachievement and New York's widening divisional lead, 2012 may not be the greatest representation of the brutally competitive nature that this rivalry traditionally embodies. But that doesn't mean the two sides aren't primed to entertain. 

So with the series set to renew this Friday in the Bronx, what better time to review arguably the most historic rivalry in all of sports? 

Take a look at some the most entertaining moments courtesy of the Yankees and Red Sox.

First Postseason Matchup: 1999 ALCS

Through the first 90-plus years of the rivalry, it was hard to believe the Yankees and Red Sox hadn't played one truly meaningful game. 

But that all changed in 1999 when the two squared off in the ALCS, marking the first official playoff game between baseball's bitterest foes. 

New York was fresh off a World Series title, and Boston's championship drought exceeded 80 years. 

And from game one, it was clear that those trends weren't changing. 

A 10th inning walk-off home run from Bernie Williams set the tone for New York in a series they would end up winning in just five games. 

But even in the one-sided-affair, story lines weren't too tough to come by. 

Game 3 appeared promising when Roger Clemens and Pedro Martinez were announced as the probable starters. But the pitchers' duel turned into a pounding, and the Red Sox won by a score of 13-1 at Fenway. 

The Sox chased Clemens after just two innings of work, and Pedro struck out 12 batters en route to the most lopsided playoff victory in Red Sox/Yankees history.  

Benches Clearing

With a potential Red Sox/Cubs World Series looming, tensions were high during the American League Championship series in 2003. 

It had been 85 years since their last championship, and Boston entered the series as the favorite over a powerful Yankee lineup. After falling to the Bronx Bombers in their first postseason matchup four years prior, it was clear the Red Sox weren't going to surrender so easily this time around. 

Game 3 of the 2003 LCS was just the tip of the iceberg.  

The benches first cleared when Pedro Martinez plunked Karim Garcia in the top of the fourth inning. But an exchange of words between Roger Clemens and Manny Ramirez in the bottom half of the frame proved devastating. 

Well, at least for one man. 

Don Zimmer, then 72 years old, proved no match for the much younger Martinez when he charged the mound in fury. The Yankees bench coach ended up face down in the grass in front of thousands of heckling Fenway Fans in what would turn into one of baseball's most humiliating video clips. 

Pedro got the moment of fame, but Zimmer and New York would get the last laugh (more on this later).

The Original Playoff

Before the wild card system was implemented, the only chance for a playoff between inter-divisional opponents was game 163. 

That's what happened in 1978 when the Yankees and Red Sox engaged in one of the most memorable pennant races of all time. 

New York had overcome a 14-game, mid-July deficit in the standings to set up the sudden death playoff with Boston on the final day of the season. And with their ace, Ron Guidry (then 24-3), on the bump, the Yankees had reason for optimism. 

Shockingly, the Bronx Bombers entered the seventh inning trailing 2-0 despite another strong outing from their Cy Young award winner. 

But everything changed when Bucky Dent stepped to the plate with two outs. 

To that point in the season, Dent was batting .243 with just four home runs. But with two runners on, he turned into the unlikeliest of heroes when he lifted a 1-1 pitch over the Green Monster in left field.

The Yankees would hold on to win the one game playoff by the score of 3-2 and went on to win one of their 27 world championships. 

It may not come as a surprise that Dent was named the World Series MVP. 

Boston Massacre

Fourteen games separated the Yankees from the division-leading Red Sox in the middle of July 1978. 

Less than two months later, the gap was just four. 

Elongated stretches of poor play from the Red Sox, coupled with a late-season push by New York, created an unlikely September playoff race as panic spread rapidly throughout Boston. 

And on the seventh day of the month, the Yankees were coming to town.

Many originally viewed the four-game series at home as an opportunity to extend their lead and bury the Bombers for good.

But in fact, it would be the exact opposite. 

In what would later be labeled "The Boston Massacre", New York came into Fenway and won all four games—outscoring the Sox 42-9 in the process.

The seemingly insurmountable 14-game lead had suddenly vanished, and in the most demoralizing of fashions. 

Boston's collapse would later be completed in the 163rd game of the year.

Does the name Bucky Dent ring any bells?

"Aaron Boone Has Hit a Home Run"

For the younger Yankee fans, it is the single moment that will be forever etched in our memory. 

Jeter's picture-perfect 3,000th hit was inspiring. The final out of the 2009 World Series was fantastic. 

But nothing can top the emotions that transpired in the bottom of the 11th inning in game 7 of the 2003 ALCS.

"Aaron Boone has hit a home run! The Yankees are going to the World Series!", Charley Steiner cried from the Yankees radio booth on a chilly October night in the Bronx. 

It was like a scene from a movie—the scenario every little leaguer on the planet has dreamed about. 

And I got to watch it live. 

The moment the bat made contact with the ball, I knew it was gone. And so did everyone else. 

Fans in the bleachers began celebrating prematurely as the no-doubter sailed into the left-field seats at Yankee Stadium. 

Tim Wakefield's reaction said it all. The Red Sox pitcher who surrendered one of the most memorable home runs in Yankee history dropped his head almost instantaneously. He dropped to the ground and sat motionless on the pitchers mound, head in hands, as Aaron Boone rounded the bases in glory. 

Of course New York would go on to lose in the World Series to Josh Beckett and the Florida Marlins later that month.

But the 10-second memory gives me chills to this day. 

Comeback of the Century

It comes as no surprise that the most improbable comeback in sports history stands as the most entertaining moment from the extensive Yankees/Red Sox rivalry. 

The 2004 ALCS was all but over. With the Yankees leading the series 3-0, closer Mariano Rivera took the mound to shut the door on Boston's season and extend their championship drought to 87 years.

The fat lady was standing in the on-deck circle. And she was ready to sing. 

But Dave Roberts had other ideas. 

The pinch-runner entered the game after Kevin Millar drew a leadoff walk from the Yankee closer. Roberts wasted no time when he stole second on Rivera's first pitch to Bill Mueller. 

Roberts would be singled in moments later, and the glimmer of hope was lit. 

David Ortiz won game four with a walk-off home run in the 12th frame. And while the Sox still trailed 3-1 in the series, they had all the confidence they needed. 

Big Papi played hero again in Game 5 when a single in the 15th inning brought Boston one game closer to history. 

After Curt Schilling's infamous "bloody sock" in Game 6, the tables had turned completely. Boston carried all the momentum into a Game 7, which was highlighted by Johnny Damon's second-inning grand-slam off Javier Vazquez. 

The belief in Boston began to spread: The curse was over, and nothing could prevent the Red Sox from claiming their first World Series title in 86 years.

Not after the comeback of the century.

Not after beating the Yankees.