The Yankees and Red Sox will add a new chapter to their eternal rivalry this October.
The Bronx Bombers and BoSox will meet in the Wild Card round of the 2025 MLB Postseason, with the winner of the best-of-3 series advancing to face the Toronto Blue Jays in the American League Divisional Series.
According to the betting market, the Yankees are the more likely of the two rivals to advance.
The bookmakers at FanDuel Sportsbook tagged the Pinstripes as a -178 favorite to beat the Red Sox in the best-of-3 series, which begins on Tuesday night. Boston is +148 to advance, which equates to a 40.3 percent chance when you convert the odds to implied probability.
All three games will take place at Yankee Stadium.
| Team | Odds |
|---|---|
| Yankees | -178 |
| Red Sox | +148 |
The Yankees finished five games ahead of the Red Sox, but went 4-9 against Boston in 2025, including a stretch in which the Pinstripes lost eight in a row to their archenemy.
The Yanks are the third-favorite to win the American League pennant behind the Mariners and Blue Jays, and they are tied with the Blue Jays and Brewers for fourth-shortest odds in the World Series futures market.
Boston is 19/1 to win the World Series and +750 to win the American League.
Game 1 of the best-of-3 set takes place on Tuesday night. The Bombers are a -132 favorite to win the curtain-raiser, which features a probable pitching matchup of Max Fried against Garrett Crochet.
Carlos Rodon is slated to start Game 2 for the Yanks. The Red Sox have yet to indicate who they will counter with on Wednesday.
Michael Leboff is a long-suffering Islanders fan, but a long-profiting sports bettor with 10 years of experience in the gambling industry. He loves using game theory to help punters win bracket pools, find long shots, and learn how to beat the market in mainstream and niche sports.