Never-before-seen history? Droughts breaking? Best World Series matchups for every type of MLB fan

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  David SchoenfieldSep 28, 2026, 07:00 AM ET

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  • Covers MLB for ESPN.com
  • Former deputy editor of Page 2
  • Been with ESPN.com since 1995

With 12 teams in the MLB playoffs, there are 36 possible World Series matchups. This year's matchups give us the possibility of small-market showdowns or deep-pocketed behemoths facing off -- and the 2026 playoff field also boasts three franchises that have won a World Series and a fourth with the longest title drought in the sport.

Somewhere in there is one series for every type of fan to enjoy. Here are six matchups that would be fun to see in this year's Fall Classic, using all 12 teams.

If you like No. 1 seeds making it: Rays vs. Brewers

Since 2018, the Milwaukee Brewers are fourth in the majors in wins and the Tampa Bay Rays sixth, and although they've combined to miss the playoffs just four times in 18 seasons, the only World Series appearance came from Tampa Bay in the shortened 2020 season. The Brewers haven't been to a World Series since 1982 and remain without a championship since the franchise was born as the Seattle Pilots in 1969.

Neither team was expected to be the top team in its respective league coming into the season. The Brewers, despite having the majors' best record in 2025, were just 11th in ESPN's preseason power rankings -- perhaps understandable given they lost rotation members Freddy Peralta and Jose Quintana over the winter (and Quinn Priester then missed the entire season). Milwaukee more than held serve, leading the majors in games started by rookie pitchers while winning 100 games for the first time in franchise history.

The Rays, meanwhile, were just 21st in the preseason rankings. They overcame a seasonlong injury to Ryan Pepiot as Nick Martinez and Drew Rasmussen had great years in the rotation while Bryan Baker locked down the ninth inning and Junior Caminero powered the offense.

Combined years without a championship: 85

Five players to fill out your Immaculate Grid: Hideo Nomo, Greg Vaughn, Julio Franco, Nelson Cruz, Ben Grieve

2026 tie-in between teams: Rasmussen and Jake Bauers

The two small-market franchises operate similarly but have been frequent trade partners, making at least one trade every year since 2021. Tampa Bay ace Rasmussen came over from the Brewers as part of the Willy Adames trade in 2021. The Rays converted him into a starter, and Rasmussen has a 2.71 ERA in his six years in Tampa, battling injuries along the way but now with back-to-back 30-start seasons.

Bauers, who led the National League in on-base percentage, reached the majors with the Rays in 2018 but was traded after the season to Cleveland in a deal that returned Yandy Diaz to Tampa Bay (the Rays are so good at this stuff). Bauers eventually passed through Seattle, Cincinnati and New York before eventually landing in Milwaukee in 2024 and producing a career season this year.

Why this would be fun: Both teams are sort of outliers in this era of power ball, ranking in the bottom third in home runs, with the Brewers last in the majors for much of the season. They rank 1-2 in batting average and will deploy some old-school small ball -- the Rays led the majors in both sacrifice bunts and bunt hits while both teams finished in the top five in stolen bases. Both are also exceptional defensive teams.

The style of play on display would be enticing for fans tired of three-true-outcomes-style offense. Plus, both teams deserve to be here as the top regular-season team in their respective leagues. Since the wild-card era began in 1995, the nature of baseball's postseason makes it rare for the top seeds to meet in the World Series. It has happened just five times: 1995 (Braves over Cleveland); 1999 (Yankees over Braves); 2013 (Red Sox over Cardinals); 2020 (Dodgers over Rays); and 2024 (Dodgers over Yankees).

Best potential drama: Aside from the whole "This is the World Series that might save baseball for 2027 since it will be harder to argue the Dodgers are ruining baseball if we get this matchup of small-market teams" drama?

How about Tampa Bay catcher Liam Hicks versus the Milwaukee base stealers. Hicks has done most of the catching for the Rays since coming over from Miami at the trade deadline, but he's in the lineup for his bat, not for his throwing abilities at the plate. He has a below-average arm and the Brewers like to run, with seven players in double digits in steals.

If you want long-suffering fanbases to feel joy: Guardians vs. Padres

The San Diego Padres haven't won a World Series since joining the NL in 1969 and have been knocking on the door since 2020, making the playoffs five times in seven seasons -- but their fans' suffering is nothing compared to that of the Cleveland Guardians' fans. Cleveland hasn't won the World Series since 1948, the longest drought in the majors.

If we do get this matchup, one request: Both teams must wear 1970s throwback uniforms for one game. The same game. And we mean the Guardians wearing those all-red uniforms they wore from 1975 to 1977 and the Padres wearing those mustard yellow uniforms they wore in 1972 and 1973. It would be the all-time ugly uniform matchup ... and absolutely glorious.

Combined years without a championship: 134

Five players to fill out your Immaculate Grid: Gaylord Perry, Roberto Alomar, Dave Winfield, Oscar Gamble, Johnny Grubb

2026 tie-in between teams: Joey Cantillo/Slade Cecconi

Cantillo and Cecconi have been key parts of the Cleveland rotation all season, although both will be in the bullpen for the playoffs. Cantillo came over from the Padres in that massive nine-player trade in 2020 that sent Mike Clevinger to the Padres. Josh Naylor was also part of that deal -- and the Guardians later traded him to the Diamondbacks for Cecconi.

Why this would be fun: Just everything at stake for two franchises that have had a lot of recent success but have those long droughts -- and two more small markets to boot. Plus, we'd get great weather in San Diego and maybe the best fans in baseball -- the Padres surpassed 3.2 million in attendance for the fourth straight year.

Best potential drama: Parker Messick against Fernando Tatis Jr. and Manny Machado. This would be one of the best kinds of postseason storylines: a relatively unknown rookie -- although a very good one, going 12-9 with a 2.55 ERA and 6.2 WAR -- going against two of the biggest names in the sport.

Tatis started the season with that horrendous home run slump, not hitting one until his 56th game, but he has been one of the top hitters in baseball since late May. Machado had his worst offensive season, although he did still hit 29 home runs. Tatis has been good in his postseason career (1.114 OPS), while Machado hasn't (12 home runs in 51 games, but a .682 OPS). Messick's fastball plays above its velocity, ranking as the third-most valuable pitch of 2026 via Statcast's run value metric.

If you like deep-dish pizza and no ketchup on your hot dogs: White Sox vs. Cubs

How about the rare Chicago White Sox-Chicago Cubs Fall Classic. Aside from the many Yankees/Brooklyn Dodgers or Yankees/New York Giants showdowns, there have been just four other all-city World Series matchups:

• 2000: Yankees vs. Mets

• 1989: A's vs. Giants (close enough)

• 1944: Browns vs. Cardinals

• 1906: White Sox vs. Cubs

Ah, 1906. One of the biggest World Series upsets of all time, when the underdog White Sox -- known as the Hitless Wonders -- defeated a Cubs team that won a record 116 games. That was the last time the two faced off in the World Series. This is just the fourth time both clubs have made the playoffs in the same year -- 1906, 2008 and 2020 were the others -- and this matchup would give us the opportunity to remember Jiggs Donahue and Fielder Jones and Doc White and Three-Finger Brown and Wildfire Schulte.

The White Sox, if they get here, would have to be considered the least likely World Series team of all time. The 1991 Braves went worst to first, 97 losses to 94 wins, the current holder for most losses the year before reaching the World Series. The 2007-08 Rays went from 96 losses -- and no winning seasons in franchise history -- to 97 wins. Even the 1969 Mets had gone 73-89 in 1968. But the White Sox? They lost 121 games in 2024 and 102 in 2025. They were 28th in our preseason power rankings.

Combined years without a championship: 29

Five players to fill out your Immaculate Grid: Sammy Sosa, George Bell, Steve Stone, Goose Gossage, Bobby Bonds

2026 tie-in between teams: Will Venable

The White Sox manager began his coaching career in 2018 with the Cubs before later moving on to the Red Sox and Rangers before taking over the ChiSox in 2025.

Why this would be fun: There's always the chance the pope might throw out a first pitch.

Best potential drama: Pete Crow-Armstrong against the White Sox's pitching staff. PCA had perhaps the greatest individual season in Cubs history, a remarkable 40/40 campaign in which he was both the best offensive player in the NL and the best defensive player (via FanGraphs). In six regular-season games against the White Sox, he hit .304 with four home runs and a 1.318 OPS.

If you like a never-before-seen historical matchup: Red Sox vs. Braves

A World Series matchup between original-16 franchises -- those franchises that existed during the 16-team era from 1901 to 1960 -- is always a bonus. There are a few others we could potentially get (Guardians-Phillies, White Sox-Phillies and White Sox-Braves), but this one surprisingly has never happened: the Boston Red Sox vs. the Atlanta Braves. Even though the Red Sox have played in 13 World Series and the Braves in 10, they've never played each other on baseball's biggest stage.

Another fun historical aspect: The franchises shared a city from 1901 to 1952, before the Braves moved from Boston to Milwaukee and then to Atlanta in 1966.

Combined years without a championship: 11

Five players to fill out your Immaculate Grid: Babe Ruth, Cy Young, John Smoltz, Al Simmons, J.D. Drew

2026 tie-in between teams: Chris Sale

Sale was a key guy in Boston's last World Series title in 2018 and even got the final outs in the clinching game, striking out the side in relief to finish off the Dodgers. He signed a big extension the following spring, but then injuries set in and from 2020 to 2023, he made just 31 starts. The Red Sox, tired of his unavailability, traded him to the Braves for Vaughn Grissom, a huge misfire on Boston's part as Sale reignited his career with a Cy Young season in 2024 and another dominant season in 2026 (14-9, 2.16 ERA).

Why this would be fun: Nobody is going to call the Red Sox an underdog, but their 2026 story is amazing considering they were 32-46 on June 24. Fourteen games under .500 wouldn't quite be a record low for a team that eventually reached the World Series -- the 1914 Boston Braves were 16 games under at 26-42 before making their run to the Fall Classic -- but nobody saw this coming in late June.

The Braves, meanwhile, also had a rebound of sorts, returning to the playoffs after missing them last year for the first time since 2017. This matchup would also be a chance to see Red Sox outfielders Ceddanne Rafaela and Wilyer Abreu play defense -- the pair is as good as it gets in center and right field.

Best potential drama: Sale and Payton Tolle squaring off. How much fun would it be if these two started against each other? Sale is an intense, don't-mess-with-him-on-his-pitching-days type of guy. Now 37 years old and with 62.8 career WAR, he's a likely Hall of Famer.

Tolle is the goofy, eccentric 23-year-old rookie with the Ron Swanson mustache, already a huge fan favorite in Boston -- although he certainly matches Sale's intensity on the mound (often with more demonstrative reactions). They're at different ends of their careers, but they're also similar in this way: Both are 6-foot-6 lefties with dominant 96 mph four-seam fastballs.

If you like villains: Yankees vs. Dodgers

We'll repeat last year's comment: Haters are going to hate. No World Series matchup can come close to the star power of one between the New York Yankees and Los Angeles Dodgers: Shohei Ohtani, Aaron Judge, Yoshinobu Yamamoto, Cam Schlittler, Tarik Skubal, Ben Rice, Mookie Betts (who, by the way, had a huge September). Even the second-tier guys are future Hall of Famers, Cy Young winners and All-Stars: Freddie Freeman, Paul Goldschmidt, Gerrit Cole, Blake Snell, Kyle Tucker, Cody Bellinger, Max Muncy.

There are also intriguing rookie storylines with George Lombard Jr. (can he handle the pressure for the Yankees?) and Josue De Paula (will the September call-up and best hitting prospect in the minors even make the Dodgers' roster?). What's that you say? Payrolls? Don't talk about payrolls.

Combined years without a championship: 16 ... all Yankees

Five players to fill out your Immaculate Grid: Tommy John, Andruw Jones, Hiroki Kuroda, Kenny Lofton, Gary Sheffield

2026 tie-in between teams: Aaron Judge

Bear with us here ... we're just having some fun. The Yankees drafted Judge with the 32nd pick in the 2013 draft. The Yankees received that pick as compensation for Cleveland signing Nick Swisher as a free agent. The Yankees had acquired Swisher from the White Sox, who had acquired him from the A's, who had drafted Swisher with a compensation pick from the Red Sox for Boston signing Johnny Damon. The A's had acquired Damon from the Royals, who drafted him in 1992 with a compensation pick for losing Kurt Stillwell as a free agent. The Royals had obtained Stillwell and Ted Power in a trade with the Reds. The Reds had originally obtained Power in a trade with ... the Dodgers.

Why this would be fun: Stop. Of course it would be fun. Sure, we might not get another World Series until 2029 as this matchup of the sport's giants might destroy any chance at labor peace, but the World Series could still be super, duper fun!

Best potential drama: Judge versus Ohtani (take two). Back in 2024, when both players went on to win MVP awards following historic seasons, it felt like the Showdown of All World Series Showdowns. Unfortunately, it was a dud. Judge hit .222 with one home run while Ohtani hit .105 without a home run or RBI even though the Dodgers won in five games. Both have battled injuries at the end of the regular season, and Judge's availability remains uncertain as the postseason kicks off -- but if we do get Yankees-Dodgers again, let's at least hope these two go off.

If you like teams who nearly blew it yet managed to make the playoffs anyway: Astros vs. Phillies

The Houston Astros aren't a good team, but they were good enough to win the wretched AL West with an 81-81 record. They went 18 games in September without winning two in a row -- then won their final two games of the season in a Triple-A park in West Sacramento, a fitting conclusion to this division. The weekend hero: Lucas Spence, who had gone home for the season, got called up Wednesday, hit three home runs Thursday, hit another one Saturday and then hit a big two-run triple on Sunday.

The Philadelphia Phillies, meanwhile, entered September with 99% odds of making the playoffs and a chance to still win the NL East. They quit hitting, but after a win on Tuesday, their playoff odds were still 99.1%. Then Philadelphia lost four in a row -- scoring just three runs -- and the Diamondbacks kept winning, and all of a sudden, the Phillies needed to win Sunday to clinch the final wild card.

This matchup would be a rematch of the 2022 World Series, which the Astros won in six games. They have been in slow decay since then, yet here they are, thanks to an incredible offensive campaign from MVP favorite Yordan Alvarez.

Combined years without a championship: 20

Five players to fill out your Immaculate Grid: Joe Morgan, Brad Lidge, Michael Bourn, Pete Incaviglia, Hunter Pence

2026 tie-in between teams: Garrett Stubbs

Not much here. The Phillies' backup catcher came over from the Astros in a trade following the 2021 season.

Why this would be fun: Let's put it this way: MLB would love to expand the playoffs to 16 teams, mirroring the bloated brackets of the NBA and NHL. The best chance to prevent THAT from happening -- and no real baseball fan wants a 16-team playoff bracket -- would be for an 81-81 team to win the World Series. Why play such a long season if a .500 team is going to win it all? Aside from that scenario, if the Phillies get here, Bryce Harper on the big stage, trying to win his first World Series, would be plenty of fun.

Best potential drama: Alvarez against the Phillies' staff. Alvarez was the best hitter in baseball this year -- and nobody else was really close. He led the majors in batting average (.316), OBP (.432, no one else was even over .400) and slugging percentage (.601). Watching the Phillies' big three rotation starters -- Cristopher Sanchez, Zack Wheeler and Jesus Luzardo -- attacking Alvarez at the plate will be October drama at its best.