Red Sox Chase Franchise Win-Streak Record as Yankees Look to Close Out Pirates: What Prediction Markets Are Saying

Boston is having the kind of month that makes prediction markets pay attention. The Red Sox have won 14 straight games, their second-longest streak in the 126-year history of the franchise, and they get a chance to tie and then break the club record of 15 in a single day thanks to a doubleheader against the Baltimore Orioles. Meanwhile, over in the Bronx, the Yankees are trying to close out a series against the Pittsburgh Pirates that turned into a highlight reel for one of their biggest offseason acquisitions.

Boston’s Streak Has Bettors Buzzing

The Red Sox extended their win streak to 14 games with a dramatic 6-5 win over the Orioles on Monday, capped by a go-ahead solo home run from third baseman Caleb Durbin in the eighth inning that cleared the Green Monster. That win also snapped Baltimore’s own 7-game streak, which had been the second-longest active run in MLB at the time. A rainout on July 21 pushed the two teams into a doubleheader on July 22, giving Boston back-to-back shots at history in the same afternoon and evening.

Durbin has been the engine behind the surge. He’s hitting .351 over his last 10 games with 2 home runs, 5 RBI, 2 stolen bases and 8 runs scored, and since June 19 he’s batting .304 with 9 home runs and an .894 OPS as Boston has gone 22-5 over its last 27 games, its best stretch since the 2018 World Series season. The Red Sox have climbed from last place in the AL East to within 4 games of the Yankees and sit at 51-48.

Prediction markets have consistently priced Boston as the favorite in this series, and it’s not hard to see why once you look at what Baltimore is working with. The Orioles are dealing with a lengthy injury list that includes closer Ryan Helsley (elbow, out until late August), starter Chris Bassitt (back, out until early August), catcher Adley Rutschman (wrist, expected back around July 29), infielder Blaze Alexander (fractured hand) and multiple players out for the season, including Jordan Westburg and Keegan Akin, both recovering from Tommy John surgery. Catcher Samuel Basallo is considered probable for July 22 despite shoulder discomfort, but the depth chart behind him is thin.

Yankees Look to Close Out Pittsburgh

Across town in the AL East race, the Yankees have their own series to finish up, hosting the Pittsburgh Pirates for a three-game set that wraps up July 22. New York took Game 1 8-5 behind a monster night from second baseman Jazz Chisholm Jr., who homered in back-to-back at-bats off Pirates starter Braxton Ashcraft, a first-time All-Star this season, and drove in 5 runs. Ashcraft, who came in with a strong 3.49 ERA and a 1.11 WHIP, was tagged for 7 earned runs on 9 hits over just 3 innings.

Chisholm’s season line sits at .228 with 16 home runs, 43 RBI and 26 stolen bases, a bit of a step back from his 2025 debut in pinstripes, but the multi-homer game against Pittsburgh was a season-high RBI night and a reminder of the ceiling he still carries. The Yankees improved to 56-44 with the win and remain in second place in the AL East behind Tampa Bay.

The rubber match on July 22 is a genuine pitching matchup, with Gerrit Cole taking the ball for New York against Mitch Keller for Pittsburgh, a rematch of two of the more established arms in either rotation. It’s the first meeting between these two clubs all season, and with the Yankees already up 1-0 in the set, the closing line has consistently leaned New York’s way.

What the Markets Are Saying

Put both series side by side and the story markets are pricing in is pretty simple: Boston’s momentum and Baltimore’s battered pitching staff have made the Red Sox a market favorite in a series that would have looked unthinkable a month ago, while the Yankees’ offensive firepower has them positioned to finish off Pittsburgh even with a true ace-caliber matchup on the mound in the finale. If you’re tracking MLB odds for either series, both lines reflect just how quickly things have shifted in Boston’s favor since mid-June, and how much a five-RBI night from Chisholm can move a short series’ outlook against Pittsburgh.

For bettors following along on the MLB betting guide, this stretch is a good example of why in-season form and injury reports move markets as much as raw season records do. Boston’s win streak isn’t just a hot stretch; it’s a full-team turnaround built on Durbin’s bat and a bullpen catching fire at the same time Baltimore’s pitching depth has been gutted by injuries.

Where This Leaves Things

Both series carry real stakes beyond the daily result. Boston is chasing a franchise record and climbing back into the thick of the AL East race, while the Yankees are trying to hold their ground in a division that’s tighter than expected with Tampa Bay currently on top. Prediction markets will keep adjusting in real time as the Red Sox take the field twice on July 22 and as Cole and Keller face off in the series finale at Yankee Stadium, but for now, momentum and health are doing most of the talking in how these lines are set.