October is the time when teams with real weaknesses get exposed. Just last postseason, we saw the scrappy Brewers get eliminated because they couldn't string enough hits together against elite pitching. Time and time again, we've seen the Yankees strike out a ton in October, unable to slug their way to a World Series title.
Running into a bad matchup can be what exposes these weaknesses. With that in mind, here's a look at one matchup every postseason team would love to avoid.
Atlanta Braves
Nightmare matchup: San Diego Padres
Many Atlanta Braves fans fear the Philadelphia Phillies the most, and that makes sense given their recent head-to-head history in the postseason, but the Braves have played very well against Philadelphia this season and they've had a lot of trouble with the San Diego Padres in recent history as well.
Not only did Atlanta get swept in the 2024 Wild Card Series by San Diego with much of this core intact, but they also lost the season series against the Padres this year and haven't beaten them in a season series since 2021 - the year in which they last won the World Series. The Padres, for whatever reason, have had the Braves' number.
And they happen to be incredibly talented as well. Their bullpen, led by Mason Miller, is as good as any. Their rotation, with Casey Mize and Robbie Ray added at the deadline and Nick Pivetta back from injury, is much improved. Their lineup, with Fernando Tatis Jr. and Jackson Merrill looking more like their star selves, is scarier now than it was earlier in the year. The Padres can be trouble for anyone, but especially the Braves, and that's not great, since, the way things look right now, the Padres are likely to be Atlanta's first-round matchup.
Boston Red Sox
Nightmare matchup: New York Yankees
I can picture it now. Cam Schlittler finds something to get upset about before Game 1 of a potential Wild Card Series and throws another eight scoreless innings. The Boston Red Sox would then have to deal with any combination of Max Fried, Gerrit Cole and Carlos Rodon for the next two games. Oh, and while Aaron Judge is banged up again, it doesn't sound like his latest injury is one that the Yankees are concerned about impacting his October availability.
The last thing the Red Sox should want is to face arguably the best rotation in the sport on a team that also has the best hitter in the world when healthy, yet that's the likeliest outcome for Boston right now. I actually think the Red Sox can hold their own against the Yankees, but holding their own and beating them are two different things. It's hard not to predict this series to play out similarly to the one that did just last year.
Chicago Cubs
Nightmare matchup: Milwaukee Brewers
The Chicago Cubs lost nine of their 13 matchups against the Milwaukee Brewers this season, and they've gone 16-23 in the regular season against their NL Central rivals since hiring Craig Counsell ahead of the 2024 campaign. Oh yeah, the Brewers were the team that eliminated the Cubs in the NLDS just last season.
The Brewers have the best record in the majors and would get to start arguably the best pitcher in the sport, Jacob Misiorowski, twice in a best-of-five series. Good luck beating that! Even if the Cubs are able to score runs, can they contain Jackson Chourio, who has an OPS over 1.000 and four home runs in 13 games against Chicago this season? The Brewers are better than anyone gives them credit for, and always seem to give the Cubs fits.
Chicago White Sox
Nightmare matchup: Boston Red Sox
Not only were the Chicago White Sox swept in their season series against the Boston Red Sox, but they were outscored 45-15 in those six games. They allowed an average of 7.5 runs per game and scored just 2.5 runs per game themselves. Is that good?
The regular season is just that, but it'd feel like the White Sox are overmatched on paper, too. The Red Sox would be able to field a postseason rotation consisting of the likes of Sonny Gray, Payton Tolle, Ranger Suarez and Jake Bennett while the White Sox would respond with Sean Burke and a whole bunch of openers? Is that good? The White Sox have defied the odds all year, so perhaps they can do it again, but I wouldn't trust them to beat this Red Sox team in October.
Cleveland Guardians
Nightmare matchup: New York Yankees
Cleveland Guardians fans are used to this by now. They've run into the New York Yankees four times in the playoffs since 2017 and they've lost each time. They most recently lost in five games against New York in the 2024 ALCS. Both of these teams are different in 2026, but it's hard to ignore history.
It's especially tough because the Yankees won the season series four games to two and have an AL-best +136 run differential. In contrast, the Guardians are at a -7 run differential. The Yankees have been the better team all year, they're more talented, they won the season series and they have a history of owning Cleveland in October. I wouldn't want any part of them if I were a Guardians fan.
Houston Astros
Nightmare matchup: Tampa Bay Rays
In a way, the Houston Astros and the Tampa Bay Rays are somewhat similar. Both of these teams is led by an MVP-caliber position player, with the Astros having Yordan Alvarez and the Rays being led by Junior Caminero. Both of these teams have lockdown closers, with Josh Hader and Bryan Baker being trustworthy late in games. Both of these teams have bona fide aces as well, in Hunter Brown and Drew Rasmussen.
Where the Rays should have the Astros worried is that their depth is better. Their rotation, especially if Shane McClanahan can return for the postseason, is better. Their lineup, thanks to Chandler Simpson, Jonathan Aranda, Liam Hicks and Yandy Diaz, is arguably deeper, even with a suspect lower-third. Their bullpen is also just better.
Los Angeles Dodgers
Nightmare matchup: Atlanta Braves
The Los Angeles Dodgers shouldn't really fear anybody in the postseason as back-to-back World Series champions, but if I had to pick a tough opponent, it'd be the Atlanta Braves. We've seen what the Braves can do to the Dodgers this season, as they won five of six during the regular season against L.A. including a series sweep in August. As if that isn't impressive enough, the Braves held the Dodgers to just 15 runs in six games.
Chris Sale allowed just two earned runs in 16 innings against the Dodgers, including a complete game shutout his last time out against L.A. The Dodgers would probably need to deal with him twice in a best-of-five series and potentially three times in a best-of-seven. There're questions about the rest of the Braves' rotation, but their bullpen is quite good, and their lineup, especially if Ronald Acuña Jr. and Matt Olson get going, can absolutely go toe-to-toe with the Dodgers.
Milwaukee Brewers
Nightmare matchup: Los Angeles Dodgers
The Milwaukee Brewers had the best record in the majors in 2025, yet were utterly humiliated in the NLCS by the Dodgers, getting swept and not scoring more than one run in any of the four games. They were outscored 15-4 in the four games. I'm not here to say it'll be that bad, but has anything really changed to make you believe the Brewers will beat the Dodgers in the postseason?
The Brewers are still a team centered around small ball and defense. Winning with that formula can work, but it's difficult to string hits together against elite pitching. Say what you want about the Dodgers' lineup, but their rotation is absurd. Yoshinobu Yamamoto is still there, as are Blake Snell and Tyler Glasnow. Oh yeah, Tarik Skubal is a Dodger, too. Shohei Ohtani almost certainly won't be pitching, but does that really matter, especially if the Dodgers can get his bat in their lineup?
New York Yankees
Nightmare matchup: Tampa Bay Rays
The Red Sox aren't a dream matchup by any means for the New York Yankees given their glut of left-handed pitching options, but what about the Tampa Bay Rays? The Yankees have had a tough time with the Rays this season, losing six of nine games in the regular season, and the Rays feel like the more well-rounded team on paper than Boston.
The Rays are a scarier team offensively, thanks largely to Caminero and the top of their order. The rotations are pretty similar, but Drew Rasmussen might be the scariest option of all on both teams, and he's a Ray. Not to mention, the Rays are a whopping 53-25 at home, and for the Yankees to go through Tampa Bay, they'd likely have to win at least one game at Tropicana Field. Good luck with that.
Philadelphia Phillies
Nightmare matchup: Chicago Cubs
If the Philadelphia Phillies are going to go far in the playoffs, they'll need their rotation, led by Jesus Luzardo (if healthy), Cristopher Sanchez and Zack Wheeler, to carry them there. Two of those three starters are left-handed. Guess which team is the best against left-handed pitching? That'd be the Chicago Cubs, who have an MLB-leading 123 wRC+ against southpaws this season. For those saying that Pete Crow-Armstrong is left-handed, sure, but his .903 OPS against lefties is nearly as good as his .981 mark against righties.
The Cubs match up against this vaunted Phillies rotation better than any other team in the majors, and they won six of the seven regular season matchups, outscoring Philadelphia 55-to-33 in the process. The Cubs look like a team more than capable of eliminating Philadelphia, and those two clubs are likely to face off in the Wild Card Series with how the standings look.
San Diego Padres
Nightmare matchup: Los Angeles Dodgers
There's nothing that San Diego Padres fans would like more than to eliminate the Dodgers in the postseason. They actually did so in 2022 and came awfully close to doing so in 2024 as well, so it can be done, but will it really happen? If the regular season is any indication, probably not. The Dodgers have won seven of their 10 matchups against the Padres, outscoring them 50-32 in the process.
Ultimately, I have little faith that the Padres can hit enough against this Dodgers rotation. Yoshinobu Yamamoto has allowed three runs in 20 innings of work against the Padres this season. The Dodgers should have Blake Snell and Tyler Glasnow in their postseason rotation, and they, of course, have Tarik Skubal as well. I'll believe in San Diego when I see them beat the Dodgers.
Tampa Bay Rays
Nightmare matchup: Boston Red Sox
The Tampa Bay Rays have a winning record against four of the five current postseaason teams in the American League, with the Boston Red Sox as the lone exception. Their 5-5 record against Boston isn't bad, obviously, and the Rays can still win the season series against them by winning two or three of three against Boston later this month, but the Red Sox have played them tough.
When these teams last played each other, the Red Sox outscored the Rays 28-10 in a four-game sweep at Fenway Park. The Red Sox need to prove they can win in Tampa Bay and those four games were during Boston's torrid 32-5 run, but with Roman Anthony now back and Garrett Crochet looking to return in relief for the playoffs, the Rays should watch out for their AL East rivals.
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