Yankees and Red Sox have played 20 times since spring 2025. The record is exactly even — 10 wins each. And almost nothing about how those 20 games actually played out feels even.
Boston went 9-5 against New York in the 2025 regular season and looked like the better baseball team for six months running. Then the Wild Card Series arrived, the Yankees lost Game 1, and everything turned. New York won Games 2 and 3, advanced to the ALDS, and rolled into 2026 having won five in a row against the team that had owned them all summer. The 10-10 in the scoresheet is real. So is the swing.
Here's what the last 20 actually look like, broken into the three eras inside them.
Era 1: Boston owns the marathon (2025 regular season)
The 2025 regular season was as one-sided as the Boston-New York series gets in this era. The Red Sox won the season series 9-5 across 14 games — their best head-to-head result against the Yankees in years and the foundation of an AL East push that landed them a Wild Card spot.
They won the way Boston has historically won this rivalry: starting pitching depth, contact at the top of the order, and one or two games that didn't feel close at all. The August 23, 2025 meeting at Yankee Stadium was the loudest of those — Boston 12, Yankees 1, a result that contributed to the perception that the Red Sox had simply outclassed New York for the year.
Overall record across the last 20 meetings.
Boston's edge in the 2025 regular season.
The Yankees' current streak since the 2025 Wild Card.
Boston going 9-5 in 14 games is a 64% win rate. Across a full season, that pace would have been one of the most dominant single-rivalry stretches of the decade. Through six months, the Red Sox had every right to feel like the team that had figured out the matchup.
Era 2: The Wild Card flip (October 2025)
Three games changed everything.
Game 1 of the 2025 AL Wild Card Series at Yankee Stadium went exactly the way Boston's regular season had gone. Garrett Crochet retired 17 consecutive Yankees, Masataka Yoshida came off the bench to deliver a two-run pinch-hit single in the ninth, and the Red Sox left the Bronx with a 3-1 win and a 10-4 record against New York for the year. The Game 1 winner had advanced in all 12 previous Wild Card Series. Boston was halfway home.
Then the rivalry remembered what it was. The Yankees took Game 2, set up a winner-take-all Game 3, and gave the ball to a 24-year-old rookie nobody outside New York's organization had circled as the moment-defining pitcher. They were wrong about that.
Cam Schlittler's Game 3 masterpiece
Rookie right-hander Cam Schlittler — a Walpole, Massachusetts native who grew up a Red Sox fan — struck out 12 in eight innings against his hometown team, allowing five singles and no walks while touching 100 mph late. The Yankees won 4-0, advanced to the ALDS, and pulled ahead 14-13 in postseason games between the two franchises for the first time in two decades. Bucky Dent threw the ceremonial first pitch on the 47th anniversary of his 1978 tiebreaker home run. Nothing about the symbolism was accidental.
The Yankees became the first team to lose Game 1 of a best-of-three Wild Card Series and still advance since MLB expanded the round in 2022. The season-long story of who was the better team got buried under the only three games that decided who kept playing.
Boston kept winning the bigger sample. New York kept winning the bigger moment.
Era 3: The 2026 hangover (April sweep at Fenway)
The Wild Card loss should have been a contained event. Boston still had its rotation, its lineup, its manager. The Yankees were a wild-card team that beat them in three games. New offseason, new chapter.
It hasn't played out that way.
The Yankees opened the 2026 season as the AL's best team. The Red Sox opened 2-8, climbed to 9-13, and welcomed New York into Fenway in April still searching for an identity. The series turned ugly fast. New York swept the three games — capped by a 4-2 win on April 23 in which Connelly Early, Boston's young left-hander making his first start against the Yankees since taking the loss in Game 3 of the Wild Card, was hung with another defeat after some shoddy defense behind him.
Two days later, Boston fired manager Alex Cora after a 10-17 start. Worcester Red Sox manager Chad Tracy was named interim. The team that beat the Yankees nine times in 2025 now looks nothing like the team that did it.
The two faces of this rivalry
Strip the calendar back and you can see the same matchup behaving like two different teams depending on context.
Six-month, 162-game team
Three-game, win-or-fly-home team
Neither version is wrong about the matchup. Boston really was the better team across a 14-game regular-season sample. New York really has been the better team across every game with a knife to its throat since. The honest answer to "who's better right now" depends entirely on which version of the rivalry you mean.
Key games from the last 20
Not every game in a 20-meeting window matters equally. These are the ones that did most of the work in shaping the current pattern.
What history says to expect next
The two teams meet again June 5–7 in New York and June 25–28 in Boston before the All-Star break. Recent history hands each side a clear lane.
What Boston needs to flip
- Stabilize the rotation past Crochet. The 2025 strength was depth, not the top.
- Stop giving runs away. The 116 errors in 2025 were a league-high and a Game 3 contributor.
- Find offense in the middle of the order beyond Contreras.
- Win first. Punching back from down 0-2 in a series is a different sport.
What New York needs to hold
- Keep Schlittler on the postseason map. He's now a part of the rivalry's identity.
- Manage Aaron Judge's contact rate. He's the lineup's gravity well.
- Lock down the late innings. Weaver wobbled in Game 1 — that can't be the pattern.
- Treat every Boston series like October. That's been the difference.
The honest read: Boston has the season-long playbook. New York has the moment-by-moment one. Both versions are real. Both have won. The next 20 meetings will turn on which version shows up more often when the games count.
Frequently asked questions
Who has won more in the last 20 Yankees vs Red Sox meetings?
The last 20 meetings are split exactly 10-10. Boston won 9 of 14 regular-season games in 2025; the Yankees won the 2025 AL Wild Card Series 2-1 and swept the first three meetings of the 2026 season at Fenway. The Yankees are currently on a five-game winning streak in the rivalry.
Who won the 2025 AL Wild Card Series between the Yankees and Red Sox?
The Yankees won the 2025 AL Wild Card Series 2-1. Boston took Game 1 3-1 behind Garrett Crochet, but New York responded with a win in Game 2 to force a deciding Game 3, in which rookie Cam Schlittler struck out 12 in eight innings of a 4-0 victory. It was the first time in the best-of-three format that a team had lost Game 1 and still advanced.
Why was Alex Cora fired by the Red Sox in 2026?
Alex Cora was fired on April 25, 2026 after Boston's 10-17 start to the season, capped by a three-game sweep at Fenway against the Yankees. Worcester Red Sox manager Chad Tracy was named interim manager. Boston went on to fall to 12-19 in the days that followed.
Who is Cam Schlittler and why is he now part of Yankees-Red Sox lore?
Cam Schlittler is a Yankees right-hander who debuted in July 2025. A Walpole, Massachusetts native who grew up a Red Sox fan, he started Game 3 of the 2025 AL Wild Card Series and struck out 12 in eight innings of a 4-0 win, sending New York to the ALDS. It was his 15th career major league start and one of the most dominant pitching performances in the postseason history of the rivalry.
When do the Yankees and Red Sox play next in 2026?
The teams meet next from June 5 to June 7 at Yankee Stadium, then again from June 25 to June 28 at Fenway Park, with both series falling before the All-Star break. New York carries a five-game winning streak into the June matchup.
True Sports Fan read
Watch the next Yankees–Red Sox series through one question: which version of Boston shows up? If the 2025 regular-season team finds itself again, this rivalry tightens fast. If the 0-3-at-Fenway, manager-fired version keeps lingering, the Yankees' five-game streak doesn't stop at five.