While some of the greatest World Series’ of all-time have been played since 2000, fans have still missed out on a few incredible matchups.
With the Los Angeles Dodgers securing their second consecutive National League pennant as the American League Championship Series nears its end, baseball fans across the globe are turning their eyes towards the 2025 World Series.
The culmination of a 162-game regular season and taxing postseason, the sport’s most coveted team trophy awaits at the end of a best-of-seven championship series long regarded as the stage that legends are made on.
First played in 1903, the World Series has been played in every year but two since then (1904 and 1994), with so many of the sport’s most iconic moments and games taking place during the Fall Classic.
While baseball and the World Series itself are both very old, there is no doubt that some of the sport’s most recognizable moments have already occurred in the 25 years since the turn of the century. From Mr. November and the seven-game walk-off thriller of 2001 to the Chicago Cubs breaking the Curse of the Billy Goat in 2016, fans have already been witness to incredible moments and games in recent years.
Yet not every World Series is a blockbuster, with some seasons posing a matchup between two unexpected teams while leaving fans of big-market favorites scratching their heads amid October heartbreak.
As this year’s World Series nears, here’s a look at four World Series matchups since 2000 that didn’t end up happening, but would have been thrilling series’.
In this list, I will only be including teams that advanced to that year’s League Championship Series, highlighting matchups that were a single round away from happening. This means no mention of some first-round heartbreakers such as the 2008 Chicago Cubs and 2022/2023 Los Angeles Dodgers.
1. Seattle Mariners vs. New York Mets, 2000
While it may be a hot take to kick this off by debating against the Subway Series that happened in 2000, I also think it’s fair to say that the Subway Series itself fell well short of expectations as the Yankees won that year’s Fall Classic in five games.
Perhaps a more riveting matchup for the 2000 Mets would have been the Seattle Mariners, who lost to the Yankees in six games in the ALCS. While the Ichiro-led 116-win 2001 team is remembered more by baseball fans, the 2000 team had arguably a more intriguing roster.
This is most obvious in regards to Álex Rodríguez, who was playing his final year for the Mariners in 2000. By bWAR, this was A-Rod’s finest season of his career, posting an MLB-best 10.4 WAR with 41 home runs, 132 RBI, 134 runs scored and a .316/.420/.606/1.026 slash line.
On top of having a peak A-Rod at shortstop, 2000 was also one of the strongest seasons of Edgar Martínez’s career, with the legendary designated hitter driving in an AL-best 145 runs. The lineup was further supplemented by on-base machine John Olerud, a young Mike Cameron and midseason acquisition Rickey Henderson, ironically acquired from the Mets.
The Mets boasted a lineup headlined by a prime Mike Piazza and Edgardo Alfonzo at the peak of his career, while clearly posing an advantage over Seattle in regards to the starting rotation. Lefties Al Leiter and Mike Hampton served as a formidable 1-2 punch, starting ahead of Bobby Jones and Rick Reed, each of whom mostly held their own.
This series would have put one of baseball’s best lineups of the era against a strong rotation and roster headlined by a Hall of Famer in the middle of his prime. The Subway Series was fun, but this had the potential to be a true all-timer of a World Series had it occurred.
2. Boston Red Sox vs. Chicago Cubs, 2003
Obviously a Cubs fan was bound to include the North Siders on this list, but if there were to be any series that trumped the circumstances behind the 2016 World Series between the Cubs and the then-Cleveland Indians, this would have been it.
While both of these teams were five outs away from a pennant before squandering late leads in clinching opportunities, this matchup would have featured two of the sport’s most recognized and historic franchises in the midst of the sport’s two most recognizable curses.
At the time of the 2003 postseason, the Cubs had been without a World Series title in 95 years, while the drought associated with Boston’s Curse of the Bambino had lasted 85 years. Beyond the sheer insanity of both teams’ droughts, this would have been one hell of a series.
This series would have been a true battle of firepower between a historically good offense from Boston and a flame-throwing young rotation from Chicago. The Red Sox set the MLB record for most extra-base hits in a season in 2003, and held the record for the highest team slugging percentage until the 2019 Houston Astros and Minnesota Twins surpassed them.
Meanwhile, the Cubs were spearheaded by the All-Star pitching duo of Mark Prior and Kerry Wood, with Carlos Zambrano and Matt Clement providing an excellent back half of the rotation. The Cubs also had a lineup that could pack a punch in their own right, with Sammy Sosa, Moises Alou and Aramis Ramírez leading the way offensively.
While the Yankees and Marlins still offered an excellent six-game World Series in 2003 that featured an incredible amount of drama, it feels like nothing could have surpassed the potential the Red Sox and Cubs had for this World Series.
3. Boston Red Sox vs. Los Angeles Dodgers, 2008
While this inclusion of the Red Sox wouldn’t at all feature the drama of the Curse of the Bambino, considering they won it all in both 2004 and 2007, this matchup would have featured a palpable amount of drama for a completely different reason – Manny Ramírez.
After spending over seven seasons with the Red Sox in a tenure that saw him establish a reputation as a postseason hero, Ramírez was dealt to the Dodgers at the 2008 trade deadline in a three-team deal that sent Pittsburgh Pirates star Jason Bay to Boston.
The aftermath of the deal was immediately apparent – Ramírez went on perhaps the biggest tear of his career, slashing .396/.489/.743/1.232 over 53 games with the Dodgers to close out the season, enough to finish fourth in NL MVP voting despite playing just roughly a third of his season in the senior circuit.
In addition to the drama provided by Ramírez alone, the matchup would have had plenty more to offer – a meeting of two historic franchises at markedly different places in their clubs’ histories. The Red Sox would be seeking their third World Series title in just five seasons to cement a dynasty, while the Dodgers would be searching for their first championship in 20 years as they looked to kick off a new era of their team’s history.
Ten years after this series didn’t come to fruition, the Red Sox and Dodgers did meet in the Fall Classic with wildly different rosters as Boston won the clash in just five games.
4. Detroit Tigers vs. Milwaukee Brewers, 2011
Setting aside my personal disdain for the Brewers, this is a matchup that may feel extremely random while having the potential to be an all-time classic.
Plenty of the boxes were checked going in – the Tigers had been without a World Series title since 1984, while the Brewers, established in 1969 as the Seattle Pilots, were searching for their first championship (both droughts remain ongoing).
Additionally, in a rarity for a World Series matchup, there’s established history. The Brewers spent their first 29 seasons of play in the American League, sharing a division with the Tigers for the vast majority of that time.
Beyond the shared history, regional proximity and mutual lack of recent success, this series would have also featured some of the generation’s brightest stars playing at their prime.
Milwaukee was armed with a high-octane offense headlined by two of the top three NL MVP finishers that season, with winner Ryan Braun and third-place finisher Prince Fielder as the two sluggers combined for 71 home runs.
The Brewers’ rotation was also nothing to sneeze at, with sub-4 ERAs across the board from Randy Wolf, Yovani Gallardo, Shaun Marcum and Zack Greinke.
Detroit could have countered with plenty of star power themselves, none more apparent than that of Miguel Cabrera and Justin Verlander. Cabrera hit an MLB-best .344 while leading all of baseball with 48 doubles, while Verlander won the AL MVP award on the heels of a 24-win season that saw him pitch 251 innings with a 2.40 ERA.
While the 2011 World Series was undoubtedly one of the greatest of all-time featuring one of the sport’s most dramatic games, and I’m not at all arguing that it was a bad series or should be replaced, the Brewers and Tigers of 2011 had the potential to create an equally fantastic matchup.
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