Some of the greatest Fall Classics of all time have taken place after the turn of the century, but there has certainly been a few duds as well.
The stage for the 2025 World Series is officially set, with the Toronto Blue Jays, who hope to win their first title in 32 years, taking on the Los Angeles Dodgers, who aim to become the first team since the 1998-2000 New York Yankees to repeat as champions.
This year’s World Series marks the 26th Fall Classic played in the 21st century and the 121st edition of the series overall, continuing the legacy of the longest held championship event in North American professional sports.
The best-of-seven series provides plenty of room for momentum changes and drama, with superstars and unlikely heroes alike shining in the biggest moments of their careers.
While baseball is over a century-and-a-half old, some of the sport’s most iconic moments have taken place in World Series games played over the past 25 years. From Luis Gonzalez’s walk-off single in Game 7 of the 2001 Fall Classic to the Cubs breaking the curse in 2016, games and plays indelibly etched into the minds of all baseball fans are from the new millennium.
Yet not every World Series is a classic, and not every postseason sees its greatest and most recognizable moments happen in the Fall Classic. Take the 2012 season for example, a postseason that featured four incredible League Division Series’ before also including a 3-1 comeback for the San Francisco Giants in that year’s NLCS. From there, the Giants swept the Tigers in what was a relatively uneventful and forgettable World Series.
When those biggest moments do happen to occur in the World Series though? That’s what baseball is all about – where Hall of Fame legacies are secured and memories shared across an entire generation are taken in for years to come.
With the 2025 World Series commencing this weekend, I took a look at each Fall Classic from the 21st century so far and ranked them from worst-to-best based on overall excitement and memorability.
As a minor spoiler, this list is pretty linear in the sense that every sweep is ranked below every five-game series, which is ranked below every six-game series and so on. While I was tempted to make an exception in one instance, I feel like it’s a rule of thumb that mostly holds true when remembering playoff series’.
Below is a look at how each year’s series personally shakes out for me as a lifelong baseball fan:
25. 2007 World Series: Boston Red Sox over Colorado Rockies 4-0
Unfortunately for the 2007 Fall Classic, the circumstances and series’ leading up to the World Series turned out to be much more eventful than the series itself.
While the Red Sox had just completed a 3-1 comeback against the Cleveland Indians in the ALCS, the Rockies entered the series with a perfect playoff record, having swept the Philadelphia Phillies and Arizona Diamondbacks in the NLDS and NLCS, respectively. This was, of course, also after Colorado won 13 of their final 14 regular season games and a one-game playoff against the San Diego Padres to even make it into the postseason.
The Rockies’ magical run came to a screeching halt in Game 1 of the World Series, with Josh Beckett and the Red Sox blowing away Colorado with an emphatic 13-1 victory that set the tone for the series. While Game 2 was more competitive, Curt Schilling put on a herculean effort in the final game of his career to lead Boston to a 2-1 victory and 2-0 series lead.
Game 3 was easily the most entertaining game of the series, which saw an early 6-0 Boston lead shrink to a 6-5 advantage in the late innings largely thanks to a three-run shot from 2007 NL MVP runner-up Matt Holliday. Boston ultimately pulled away in the late innings, however, and won Game 3 by a score of 10-5.
The clincher wasn’t a total snoozer, as Jon Lester put up 5.2 shutout innings while Rockies’ starter Aaron Cook offered six innings of three-run ball himself. Some late offense from Colorado in the form of Brad Hawpe and Garrett Atkins home runs were not enough, with an eighth inning pinch-hit solo shot from Bobby Kielty in what was the final at-bat of his career proving to be the difference in a 4-3 Boston victory.
Although the series had a few exciting moments, it was ultimately a reflection of the vast power differential between the AL and NL at the time, with Boston’s star power on both sides of the field proving to be far too much for the upstart Rockies in their lone World Series appearance.
24. 2012 World Series: San Francisco Giants over Detroit Tigers 4-0
I alluded to this series in the opening segment of this post, as it unfortunately served as an anti-climactic ending to what was an incredible postseason up until that point.
The Giants entered the series with a flair for the comeback, having rallied back from a 2-0 NLDS deficit to the Cincinnati Reds and a 3-1 NLCS deficit to the St. Louis Cardinals to win their second NL pennant in just three years. As for Detroit, a hard-fought five-game battle against the Oakland Athletics was followed by a relatively leisurely sweep of the New York Yankees in the ALCS to head back to the Fall Classic for the first time since 2006.
This series felt over before it started in some ways, with a three-homer explosion from Pablo Sandoval burying Justin Verlander and the Tigers in an eventual 8-3 Game 1 loss. Games 2 and 3 saw the sheer dominance of the San Francisco pitching staff in consecutive 2-0 shutout victories. A stellar outing of seven shutout innings of two-hit ball from postseason great Madison Bumgarner was followed by 5.2 shutout innings from Ryan Vogelsong on the road in Game 3, with Tim Lincecum and Sergio Romo slamming the door out of the bullpen.
The series was saved from coming in last on this list thanks to a truly exciting Game 4, a pitcher’s duel between Matt Cain and Max Scherzer that eventually went into extra innings. With two outs and a runner on second in the top of the 10th inning, an RBI single from Marco Scutaro brought home what turned out to be the championship-winning run in Ryan Theriot as Romo retired the Tigers in order to complete a 4-3 victory and series sweep.
Though it had an exciting finish with plenty of incredible pitching performances, this series lacked the plethora of high-intensity, legacy-building moments that other series’ featured.
23. 2004 World Series: Boston Red Sox over St. Louis Cardinals 4-0
Obviously, this was a legendary series as the Red Sox ended an 86-year championship drought with an emphatic sweep over the 105-win Cardinals who featured three of the top five vote-getters in the NL MVP race.
With that said, a sweep is a sweep – there’s reason that the moments fans remember the most from the 2004 Red Sox run came in the thrilling seven-game ALCS and not in the World Series that was over in the blink of an eye.
The series looked poised to be an all-time great after Game 1, a heart-stopping back-and-forth slugfest that included home runs from Hall of Famers Larry Walker and David Ortiz. With the game knotted at 9 in the bottom of the eighth inning, a two-run shot from Mark Bellhorn that rang off the foul pole gave the Red Sox an 11-9 lead they would hang on to for a Game 1 win.
Bolstered with unprecedented momentum from their historic ALCS comeback, the Red Sox cruised from that point on, allowing just three more Cardinals runs in the remainder of the series as Curt Schilling, Pedro Martínez and Derek Lowe shut down an incredible St. Louis offense to finish off a four-game sweep.
Though remembered for its historic significance, this series was ultimately a showing of dominance from the Red Sox against a team that had decisively imposed its will on the National League the entire season.
22. 2005 World Series: Chicago White Sox over Houston Astros 4-0
For what was ultimately a four-game sweep, this was a series entertaining enough to where I strongly considered ranking it above my lowest-ranked five-game series.
Similar to 2004, this series was rich with circumstance – the White Sox aiming to break an 88-year championship drought of their own while the Astros were searching for their first-ever title after finally breaking through against the Cardinals in the NLCS.
Despite being armed with a rotation that included champions in Roger Clemens and Andy Pettitte as well as flame-throwing stud Roy Oswalt, it still wasn’t enough to dent what was a historic run from the South Siders’ rotation that had just rattled off three straight complete games to close out the ALCS against the Los Angeles Angels.
Game 1 was a run-of-the-mill 5-3 White Sox victory that saw José Contreras outduel a combined effort from Clemens and rookie lefty Wandy Rodríguez. The following game was an incredible back-and-forth battle that included two of the most iconic moments in White Sox history – a go-ahead grand slam from Paul Konerko in the seventh inning and a walk-off bomb from speedster Scott Podsednik in the ninth inning. The latter of these neutralized a two-out, two-run single from José Vizcaíno that tied the game in the top of the ninth inning, giving fans at 35th and Shields an emotional roller coaster for the ages.
Game 3 offered plenty more where that came from as the series shifted to Houston. While the Astros built a 4-0 lead off of White Sox starter Jon Garland, a five-run fifth inning explosion from Chicago rendered the hot start ineffective as the South Siders took a 5-4 lead. After a clutch two-out, two-strike RBI double in the eighth inning off the bat of Jason Lane tied the game, a lengthy extra-inning battle ensued as both bullpens held the score for several innings.
The White Sox finally broke through in the 14th inning on a home run from former Astro Geoff Blum, with Chicago later adding an insurance run before closing out a 7-5 victory on the road.
The series finale saw an incredible pitcher’s duel between Freddy García and Brandon Backe, with both righties trading performances of seven shutout innings before a two-out RBI single from Jermaine Dye in the eighth inning gave the White Sox the lone run of Game 4. The late Bobby Jenks closed out Houston in the ninth inning, securing the first title on the South Side since 1917 and concluding a thrilling four games.
21. 2006 World Series: St. Louis Cardinals over Detroit Tigers 4-1
The lowest-ranking five-game series on this list, this matchup served as an underwhelming conclusion to an underwhelming postseason, with the seven-game Cardinals-Mets NLCS serving as the lone caveat to that statement.
While Detroit had home-field advantage in the series over the surprise 83-win Cardinals, Scott Rolen and Albert Pujols both got to a young Justin Verlander in Game 1 while Anthony Reyes pitched eight innings of two-hit ball in a 7-2 St. Louis victory.
Detroit answered back with a 3-1 Game 2 victory, anchored by an incredible performance from 41-year-old Kenny Rogers who allowed just two hits and three walks over eight shutout innings.
Though the series appeared to be competitive heading back to St. Louis, the Cardinals left little doubt the rest of the way. The stretch at the brand-new Busch Stadium began with eight shutout innings from ace Chris Carpenter kin a 5-0 Game 3 win, before the Redbirds erased an early 3-0 deficit and scored the go-ahead run in their last at-bat in an exciting 5-4 victory in Game 4.
Although errors played a role on both sides in Game 5, Jeff Weaver outdueled Verlander in the series-clinching game as the Cardinals never looked back after taking a 3-2 lead on a David Eckstein RBI groundout in the fourth inning. Weaver ultimately pitched eight innings, with then-closer Adam Wainwright shutting the door on Detroit to win St. Louis’ first title since 1982.
While the Cardinals were underestimated by many due to their unimpressive 83 regular season wins, a roster with multiple Hall of Famers ultimately got the job done against a Tigers team that had no answer for St. Louis’ dominant pitching, a unit that had greatly struggled sans Carpenter before the postseason.
20. 2008 World Series: Philadelphia Phillies over Tampa Bay Rays 4-1
While networks and the league were undoubtedly rooting for the Phillies to match up with the fellow east coast heavyweight Boston Red Sox, the surprise of the baseball world in the Tampa Bay Rays upset the defending champs in the ALCS to win their first-ever AL pennant.
The Phillies entered the series with plenty of momentum, coasting through the Milwaukee Brewers in four games and the Los Angeles Dodgers in five games in the NLDS and NLCS, respectively.
Though this series had plenty of potential as it featured a star-studded Phillies roster against an upstart club that didn’t feature a single household name, this Fall Classic is likely remembered by most outside of Tampa Bay and Philadelphia for the suspension of Game 5 due to inclement weather in Philly.
The Rays held home-field advantage thanks to the AL winning the All-Star game, though Cole Hamels protected an early Philadelphia lead through a stellar seven-inning performance in what was a 3-2 series-opening win for the Phillies.
Although James Shields and the Rays responded with a wire-to-wire Game 2 victory, the Phillies ended up on the right side of the series’ most exciting contest in Game 3. After Tampa Bay tied the game at 4 thanks to an errant throw from Pedro Feliz on a stolen base, Carlos Ruiz walked the Phillies off with an RBI infield hit that gave Philadelphia a 2-1 series lead.
The Phillies then turned in a dominant performance for Game 4, with a Joe Blanton home run serving as the cherry on top of a 10-2 win that put Philadelphia within a win of their first championship since 1980.
Perhaps avenging his error in Game 3, it was none other than Pedro Feliz to deliver the go-ahead single that ultimately won the Phillies the World Series in the seventh inning of Game 5. J.C. Romero and Brad Lidge went on to shut the door against the Rays, closing out a 4-3 Game 5 win and the franchise’s second World Series title.
While the Game 3 walk-off and suspension coupled with late drama in Game 5 gave fans something to sink their teeth into, this was ultimately a forgettable World Series that lacked legacy moments that are celebrated by fans across baseball for years to come.
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