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The only MLB playoff preview you need: World Series odds, likely MVPs and how far all 12 teams will go
Confirmed
In Short: The Yankees and Red Sox first met in the playoffs in 1999, with the Yankees winning in five games. In 2004, the Red Sox famously came back from a 3-0 deficit to win the World Series.
MLB experts Jorge Castillo, Bradford Doolittle, Alden Gonzalez, Jeff Passan, and David Schoenfield are readying fans for the 2026 MLB playoffs, providing odds and insights for every round.
The New York Yankees and Boston Red Sox will meet in the wild card round for the second consecutive year, with Boston securing its spot as the No. 2 wild card team.
Doolittle's World Series and matchup odds are derived from a formula using power ratings, simulating 10,000 outcomes.
The 2026 MLB playoffs feature 12 teams, with the wild card round starting on Tuesday, September 29, and the division series beginning on October 11.
The wild card round includes matchups like the Yankees vs. Red Sox, Braves vs. Phillies, and Padres vs. Cubs, with each series a best-of-three.
The National League Championship Series will start on Sunday, October 11, while the American League Championship Series will begin on Monday, October 12.
The playoffs offer a mix of Cinderella stories and long-suffering franchises, with the San Diego Padres and Cleveland Guardians among the teams hoping to break through.
Fans can watch the division series and championship series on Sling, with games airing on TBS/TruTV and FOX/FS1.
Aaron Judge of the Yankees, dealing with a calf strain, is uncertain for the wild card series against the Red Sox.
The 2026 playoffs present 36 possible World Series matchups, offering something for every type of fan to enjoy.
What this adds
The Yankees and Red Sox first met in the playoffs in 1999, with the Yankees winning the AL Championship Series in five games, a fact previously reported by WarpBeat.
The Cleveland Guardians are now aiming for their first World Series title since 1948, the longest current title drought in Major League Baseball, as previously noted by WarpBeat.
Background
The Yankees and Red Sox first met in the playoffs in 1999, with the Yankees winning the AL Championship Series in five games.
The Guardians are now aiming for their first World Series title since 1948, the longest current title drought in Major League Baseball.
What's confirmed
- Will the New York Yankees or Boston Red Sox go from a wild-card meeting to the World Series?
- The three-time AL MVP said he plans to be ready for the wild-card series despite dealing with a calf strain.
- However, the Yankees are operating as if they won't have their captain against Boston in the wild-card series.
- Here, we break down each of the 12 playoff teams' chances to win the World Series.
- It's World Series-or-bust once again for the back-to-back reigning champions, and a Dodgers three-peat would cement this team as a dynasty - while also dramatically affecting CBA talks this winter.
- 👉 Bet on MLB playoffs with theScore Bet here The Brewers won an MLB-high and franchise-record 103 games for a reason: they're a well-oiled machine.
What's still developing
- 29, as the series takes place at Yankee Stadium, like last year when New York defeated Boston in three games.
- The two teams first met in the playoffs in the 1999 AL Championship Series, with the Yankees handling the Red Sox in five games and going on to win the World Series in what was the first season superstar right-hander and then-five-time Cy Young Award winner Roger Clemens, who spent the first 13 seasons of his MLB career with the Red Sox (1984-96), was with the team.
- A series that included benches clearing in Game 3 and competitive games on the whole ended with a walk-off home run from Yankees third baseman — and now manager — Aaron Boone — to lead off the bottom of the 11th inning of Game 7 in a game where New York trailed 4-0 in the fifth inning.
- The two teams ran it back the following year (2004), but it had a much different outcome.
- After going down 3-0 in the series and giving up 19 runs on their home field in Game 3, the Red Sox became the first team in professional sports to win a series after trailing 3-0.
- Boston then went on to win the World Series for the first time since 1918.
- The 2026 MLB regular season has officially come to a close, and the MLB Playoffs are set to begin, with 12 teams ready to battle it out, with eight set to play in the Wild Card round starting tomorrow.
- Today, we are completing our final Power Rankings of the 2026 season, with these being the most important: our 2026 MLB Playoff Power Rankings.
- Without further ado, let’s start by diving into the rankings of the top teams left standing this baseball season.
- Under the new format, it can be jarring how fast that first best-of-three playoff series goes, as some of the teams who made the playoffs may not even make it to October if they get swept.
- I have ranked each of the 12 teams remaining, breaking down their chances of making a run to win it all this year.
- After the Power Rankings, you will find a graphic with the playoff bracket now that the field has been set, and we will close with my prediction for who will make it to the World Series and who will come out victorious.