With the MLB regular season heading toward its finish, the focus is quickly shifting to October. The playoff picture is taking shape, and that means it’s time to start thinking about the World Series.
Of course, there’s still a lot that can change before the postseason begins. But that doesn’t mean we can’t look ahead and imagine which matchups would make for the most exciting Fall Classic.
From familiar rivals to star-studded showdowns, there are several potential World Series matchups that would have fans glued to their screens. Here are some of the matchups we’d be most excited to see in 2026.
Los Angeles Dodgers vs. New York Yankees
It’s hard to imagine a bigger World Series than Dodgers vs. Yankees. These are two of baseball’s biggest markets, two of its most recognizable franchises and two teams that bring an enormous amount of attention wherever they play. Put them together in October and the media coverage would be off the charts.
The matchup would also be loaded with superstar talent. Shohei Ohtani, Mookie Betts and Freddie Freeman would go up against Aaron Judge, Gerrit Cole and Ben Rice. There’s also plenty of history here, with the franchises having already met 12 times in the World Series, including the Dodgers’ 2024 victory.
With both teams back in the playoffs in 2026, another Fall Classic between these two would be almost impossible to ignore.
Los Angeles Dodgers vs. Toronto Blue Jays
Could we really get a rematch of last year’s World Series? After the Dodgers and Blue Jays delivered one of the wildest Fall Classics of all time, it would be hard to turn down another meeting. The 2025 series went the distance, with Game 7 heading into extra innings before Los Angeles finally claimed the title.
The problem is getting Toronto back there could prove difficult. At the time of writing, the Blue Jays sit a game behind Cleveland for the final AL Wild Card spot, so there is still lots of work to be done. But if Toronto can make it back, the rematch would mean everything to baseball fans north of the border.
Last year’s World Series appearance captured the entire country’s attention. Another Dodgers-Blue Jays series would give fans a chance to see if Toronto could finally finish the job.
Chicago Cubs vs. Boston Red Sox
A Cubs-Red Sox World Series would bring together two historic franchises with something else in common: decades of championship frustration. These two teams spent decades carrying the weight of baseball’s most infamous championship droughts. Boston finally broke through in 2004 after 86 years without a title, while Chicago ended its 108-year wait in 2016.
That history would make a Cubs-Red Sox World Series about much more than just the two teams on the field. Both fanbases know what it feels like to wait, suffer through near misses and wonder when the next championship will finally arrive.
Now, with both clubs sitting in playoff position, they have a chance to write another chapter in their long histories. A Fall Classic between them would be a celebration of how far both franchises have come.
Tampa Bay Rays vs. Milwaukee Brewers
What if two of baseball’s biggest small-market success stories met in the World Series? The Rays and Brewers have built competitive teams without the financial firepower of MLB’s biggest spenders, making a matchup between them a pretty compelling underdog story.
Tampa Bay has long been known for getting creative with its roster and payroll, while Milwaukee has taken a similar approach to building a contender. That makes it even more impressive that both teams were the first clubs to clinch playoff spots in 2026.
There would also be plenty of talent to watch. Junior Caminero has emerged as one of the game’s biggest young stars, while Milwaukee has built a deep roster that continues to find ways to win. A Rays-Brewers World Series would be a pretty fitting reminder that you don’t need the biggest payroll to compete for baseball’s biggest prize.
Los Angeles Dodgers vs. Cleveland Guardians
Yes, we know the Dodgers have already made this list a few times. But when you’re talking about the defending champions and MLB’s biggest spender, it’s pretty hard to leave them out. A World Series against Cleveland, though, would give us a particularly fun contrast.
The Dodgers currently rank No. 1 in MLB in payroll, with a projected luxury-tax payroll of more than $400 million. The Guardians, meanwhile, rank 30th, sitting at the very bottom of the league with a payroll of just $77 million. That would make this about as close to a baseball version of David vs. Goliath as you can get.
Of course, Cleveland still has a long way to go. The Guardians are right in the middle of the AL playoff race and need to secure a Wild Card spot before they can start thinking about a trip to the Fall Classic. If they get there, taking down the Dodgers would make for one heck of a story.
New York Yankees vs. Philadelphia Phillies
New York and Philadelphia aren’t exactly known for being forgiving sports towns. Both fanbases are passionate, demanding and more than willing to let their teams know when things aren’t going well. Put the Yankees and Phillies in a World Series, and the pressure would be enormous from the very first pitch.
The long ball could be a big part of this matchup, with Judge, Harper and Schwarber all capable of changing a game with one swing. And with both teams playing in cities where the stakes are always high, the World Series spotlight would be enormous.
A World Series between these two teams would be as much about the atmosphere as the baseball. Every mistake would be magnified, every big hit would be deafening and neither fanbase would be satisfied with anything less than a championship.