The 10 Biggest On-Paper Mismatches in MLB Postseason History

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Not every postseason series is created equally. Throughout MLB playoff history, there have been some rather lopsided matchups, with the bracket pitting some 100-plus win teams against opponents that snuck into the postseason by winning a weak division or through the wild card.
We’re sure to see another on-paper mismatch in the ALCS. The Guardians and White Sox won 85 and 84 games, respectively, while the Rays were the American League’s top regular season team with 98 wins. Chicago would be an especially pronounced underdog on the heels of three straight 100-plus loss campaigns. The White Sox’ regular season winning percentage (.519) is 86 points lower than the Rays’ (.605), which is a large difference—but wouldn’t quite crack the top 10 most lopsided postseason matchups of all time.
Neither the White Sox nor Guardians should fret about the tough task in front of them should they advance to the ALCS. Only six of the 10 heavily favored teams covered in this article went on to win the series against their “lesser” opponents. In fact, three of the five relevant matchups to happen this century were won by the team with significantly fewer wins. Let’s take a look at how they all played out.
10. 2018 World Series
Boston Red Sox (108–54, .667) vs. Los Angeles Dodgers (92–71, .564)
Win percentage differential: Red Sox +103
Win differential: Red Sox +16
Series result: Red Sox win, 4–1
There was a big disparity in win totals between the 2018 World Series teams, as the Red Sox won 16 more games than the Dodgers during the regular season. Entering as big favorites for the Fall Classic, Boston took care of business as expected against Los Angeles, though they were led to victory by an unexpectedly brilliant performance from Steve Pearce, who had three home runs and eight RBIs across the five-game series to earn MVP honors.

9. 1927 World Series
New York Yankees (110–44, .714) vs. Pittsburgh Pirates (94–60, .610)
Win percentage differential: Yankees +104
Win differential: Yankees +16
Series result: Yankees win, 4–0
The hallowed 1927 Yankees were nicknamed “Murderers' Row” for a reason. With 110 wins, they were MLB’s only team with more than 95 wins. They met a 94-win Pirates team in the World Series, and quickly disposed of their opposition in a four-game sweep. New York had been to the World Series the previous season, but lost in seven games against the Cardinals. Still, they were heavy favorites against Pittsburgh in ‘27, and they lived up to the billing.
8. 2021 NLCS
Los Angeles Dodgers (106–56, .654) vs. Atlanta Braves (88–73, .547)
Win percentage differential: Dodgers +107
Win differential: Dodgers +18
Series result: Braves win, 4–2
The Dodgers won 106 games, second-most in MLB, and they met the league’s “worst” division winner in the NLCS in the 88-win Braves. Despite having 18 more wins than Atlanta during the regular season and beating them in the same round the previous year, the Braves who stunned L.A. in the series, defeating them in six games before going onto the World Series, where they also defeated the Astros in six games. That Braves team went down as one of the championship-winning clubs with the fewest regular-season wins in league history.

7. 1932 World Series
New York Yankees (107–47, .695) vs. Chicago Cubs (90–64, .584)
Win percentage differential: Yankees + 111
Win differential: Yankees +17
Series result: Yankees win, 4–0
The Yankees had the most wins during the regular season with 107, and they met a 90-win Cubs team in the World Series. New York’s dominant lineup featured six players with an OPS above .840, whereas Chicago didn’t have a single player reach that mark during the regular season. Led by the likes of Lou Gehrig and Babe Ruth, the Yankees made quick work of the Cubs, sweeping them in four games.
6. 2022 World Series
Houston Astros (106–56, .654) vs. Philadelphia Phillies (87–75, .537)
Win percentage differential: Astros +117
Win differential: Astros +19
Series result: Astros win, 4–2
The Astros had the AL’s best regular-season record and the second best record overall, trailing only the 111-win Dodgers. Meanwhile, the Phillies snuck into the postseason as the National League’s final wild-card team before making a stunning run to the World Series. Houston was, unsurprisingly, heavy favorites in their showdown against Philadelphia, having been to the World Series the previous season and having advanced to at least the ALCS in each of the five previous campaigns. The Astros got the job done, defeating the Phillies in six games.

5. 2001 ALCS
Seattle Mariners (116–46, .716) vs. New York Yankees (95–65, .594)
Win percentage differential: Mariners +122
Win differential: Mariners +21
Series result: Yankees win, 4–1
The Mariners tied the MLB record for most wins in a single season with 116. That team, led by Ichiro Suzuki, Bret Boone, Edgar Martinez and Mike Cameron, was a formidable regular-season squad but couldn’t go all the way. Up against the Yankees in the ALCS, the wheels came off for Seattle, who stumbled to defeat in a five-game set without winning a single game at home. It was the second straight year the M’s lost in the ALCS, having lost in six games to the Yankees in 2000, too.
4. 2022 NLDS
Los Angeles Dodgers (111–51, .685) vs. San Diego Padres (89–73, .549)
Win percentage differential: Dodgers +136
Win differential: Dodgers +22
Series result: Padres win, 3–1
The Dodgers were big favorites to reach the World Series, if not win it all. They were matched up with their division rival Padres in the NLDS, a team they’d defeated in 14 of 19 games during the regular season. Despite winning 22 more games than San Diego, it was the Padres that emerged victorious. L.A. won Game 1, but then stunningly dropped three in a row, losing the series 3–1.

3. 1906 World Series
Chicago Cubs (116–36, .763) vs. Chicago White Sox (93–58, .616)
Win percentage differential: Cubs +147
Win differential: Cubs +23
Series result: White Sox win, 4–2
The crosstown World Series showdown between the Cubs and White Sox was one of the biggest mismatches in MLB postseason history, and also one of the all-time great upsets. The White Sox won 23 fewer games than the Cubs, but managed to pull off a miraculous upset in the Fall Classic, defeating their rivals in six games. That Cubs team was led by legendary ace Mordecai Brown and standout first baseman Frank Chance, but they were stunned by the Ed Walsh and the White Sox, who didn’t have a single player with an OPS above .695 during the regular season.
2. 1995 ALCS
Cleveland (100–44, .694) vs. Seattle Mariners (79–66, .545)
Win percentage differential: Cleveland +149
Win differential: Cleveland +21
Series result: Cleveland wins, 4–2
In a shortened 1995 season, Cleveland was MLB’s top team with 100 wins. They led MLB in OPS (.840), home runs (207) and runs scored (840), and ranked third in ERA (3.83) and WHIP (1.31), making them big favorites against the 79-win Mariners. Despite losing two of the first three games, Cleveland managed to turn things around and secure a 4–2 series victory. They reached the World Series but ultimately fell short of a championship, losing in six games against the Braves.
1. 1998 ALDS
New York Yankees (114–48, .704) vs. Texas Rangers (88–74, .543)
Win percentage differential: Yankees +161
Win differential: Yankees +26
Series result: Yankees win, 3–0
Somewhat similar to this year, the AL East was the strongest division in the American League, and the only one with a team that won more than 90 games. The Yankees had MLB’s best record with 114 wins, and their division series matchup was against a Rangers team that won just 88. Texas had the fewest wins of any team in the postseason that year, and they were quickly brushed aside by New York in a 3–0 sweep.

Karl Rasmussen is a staff writer for Sports Illustrated. A University of Oregon alum who joined SI in February 2023, his work has appeared on 12up and ClutchPoints. Rasmussen is a loyal Tottenham, Jets, Yankees and Ducks fan.
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