Complete history of Yankees-Red Sox playoff matchups heading into 2025 Wild Card

The New York Yankees-Boston Red Sox rivalry dates back to the early 1900s. It's regarded as the most fierce in baseball and potentially all of sports. From the Curse of the Bambino to Bucky Bleepin' Dent to Aaron Boone's walk-off home run in Game 7 of the 2003 ALCS to Boston's historic 3-0 comeback in 2004, there's a lot of bad blood.

But what if we told you they didn't need in the playoffs until 1999? Crazy! It took nearly 100 years for the two teams to face off in October. Honorable mention, however? The 1978 tiebreaker Game 163 to determine the division winner. It wasn't an official playoff game, but it was the actual definition of a playoff. And that's when Dent made his mark before the Yankees went on a World Series run.

Everything else? Well within this lifetime, and very much remembered vividly by most baseball fans. And over the last 20 years, it's been all Red Sox.

Complete history of Yankees' playoff matchups with Red Sox

1999 ALCS

In the midst of the Yankees' dynasty, they matched up with the Red Sox in the 1999 ALCS. The Yanks finshed 98-64 (four games ahead of the Sox) to give them the division crown and home field advantage.

Boston was tough in the first three games, too. The Yankees escaped with narrow one-run victories in Games 1 and 2 (with Game 1 going to extras) before Boston erupted for a 13-1 win in their return to Fenway Park for Game 3. But New York was undeterred, outscoring the Sox 15-3 in the final two games to win the series in five. They would advance to the World Series and defeat the Atlanta Braves.

2003 ALCS

You know this one. It's the series that got Aaron Boone his job as manager back in 2018. The Yankees and Sox did battle and it went to seven games, with Boone walking off the Sox in Game 7 with one of the most epic home runs in franchise history against Tim Wakefield. Game 3 also featured one of the most memorable brawls in baseball history when Manny Ramirez cried about a Roger Clemens pitch that was nowhere near him. All hell broke loose, and Pedro Martinez threw 72-year-old Don Zimmer to the ground by his head, and somehow is still adored to this day. This was the height of the rivalry, without a doubt.

These teams traded barbs on the road in a hard-fought series which would set the stage for ... the absolute worst outcome in baseball history the very next year. Oh yeah, and the Yankees lost the 2003 World Series to the Florida Marlins.

2004 ALCS

The Yankees led 3-0. Game 4 featured the infamous Dave Roberts steal in the bottom of the ninth that helped tied the game, followed by the David Ortiz walk-off homer in the 12th. Game 5 went to 14 innings with the Red Sox winning 5-4.

The series went back to the Bronx. The Yankees needed to win one of the final two games on their home turf. After a close one in Game 6 (a 4-2 loss), New York got blown out in Game 7, with all the life sucked out of Yankee Stadium after David Ortiz's first-inning two-run homer and Johnny Damon's second-inning grand slam. Game 6 also featured Curt Schilling's "bloody" sock and A-Rod's glove slap on Bronson Arroyo.

There's never been a worse feeling in sports, and there might never be again. This all set the stage for the Red Sox being the best team in baseball over the last 20 years. They have the most championships since they demoralized the Yankees and captured the 2004 Fall Classic.

2018 ALDS

If not for the tainted Red Sox behavior in 2018 under all-time schemer Alex Cora, perhaps we're talking about a different outcome. But the Red Sox won a franchise-record 108 games and then breezed through the postseason en route to their fourth title since 2004. They went 11-3 on their run and handled the Yankees easily in the ALDS.

After the Bombers stole Game 2 at Fenway Park, the Sox responded with a 16-1 victory at Yankee Stadium in Game 3 — one of the most embarrassing postseason losses in franchise history. New York fans remember this one well, as Luis Severino was believed to have forgotten the start time, resulting in his awful outing (3 IP, 7 H, 2 BB, 6 ER). Brock Holt hit for the cycle. Hell on earth.

The Yankees would lose Game 4 by a run as their ninth-inning rally fell short. We'll never forgive Zack Britton for giving up a solo homer to Christian Vazquez to lead off the fourth inning, either. That ended up making the difference.

2021 AL Wild Card Game

The 2021 season featured arguably the worst Yankees playoff team when factoring in talent, missed opportunities, and the way they went out. Because they let countless games slip out of their fingertips, they ended up with the same record as the Red Sox, losing the tiebreaker because of the regular season head-to-head record. That meant Boston would have home field advantage for the one-game playoff.

Gerrit Cole was on the mound for this one, but he pitched with a bum hamstring. And it showed. He gave up a two-run homer to Xander Bogaerts in the first inning, and right then it felt like it was over. The Sox would extend their lead to 3-0 before the Yankees scored their first run of the game in the top of the sixth. Ok. It felt like they had some life.

But nope. Luis Severino and Jonathan Loaisiga tag-teamed to give up three more runs. That was it. The Yankees would eventually lose 6-2 and the Red Sox went to the ALCS. Gerrit Cole became a meme. This was the Red Sox's lone playoff appearance between 2019-2024, and they managed to make the most of it by getting the last word in against their rivals.

2025 AL Wild Card Series

Please. God.