The Yankees and Red Sox are set to play each other in the 2025 MLB Postseason for the 6th time in MLB history. The Sox and Yankees are a perfectly even 12-12 against each other in the playoffs, with the Red Sox holding a slight 3-2 edge in series wins. Furthermore, the Yankees have not defeated the Red Sox in the postseason since 2003. In honor of one of the most iconic rivalries in American sports being renewed this Tuesday when the Red Sox come to the Bronx to face the Yankees in the 2025 AL Wild Card, I decided to rank every postseason series played between the two iconic franchises.
#5 – 2021 AL Wild Card Game
The first and only time the Yankees and Red Sox faced off in the one-game wild card format was in 2021. The game was a relatively easy victory for Boston at Fenway as Nathan Eovaldi held the Bronx Bombers to 1 ER in 5.1 IP en route to a 6-2 Boston victory. Boston ended up losing to the Houston Astros in the ALCS, so this game did not have the incredible impact on baseball history as some of the other entries on this list. Probably the most iconic moment from this game was Giancarlo Stanton’s 1st inning double that Yankees’ long-time play-by-play radio announcer, John Sterling, erroneously called a home run (even as Stanton was clearly standing on second).
#4 - 1999 ALCS
Back in 1999, the Yankees and Red Sox met in the postseason for the first time (officially), with each team looking to advance to the World Series. The Yankees were coming off a World Series victory in 1996 and 1998, while the Red Sox were looking for their first World Series berth since 1986. The Yankees won the series handily 3-1, but it was intense nonetheless. The Yanks won games 1 and 2 by a combined 2 runs, and a highly anticipated Roger Clemens vs Pedro Martinez game 3 matchup surprisingly resulted in 14 runs and 24 hits as the Sox won their only game of the series. This series was fun, but the iconic matchups we have all come to love were still a few years away at this point.
#3 2018 ALDS
This series beat out the 1999 ALCS simply by how shocking it was. The Sox staved off a late comeback by New York in game 1 to secure a 5-4 victory. In game 2, the Yankees bounced back, winning 6-2 thanks to an incredible performance from Masahiro Tanaka on the hill and a 4 RBI effort from Gary Sanchez. Game 3 took a turn when the Red Sox utterly dominated the Yankees, winning by a score of 16-1. It was the biggest postseason loss the Yankees had ever suffered at home, and it completely demoralized the fan base. The Sox went on to win game 4 in the Bronx by a score of 4-3 before ultimately running the table and taking home their 4th World Series championship in under 15 years.
#2 2003 ALCS
Depending on which team you root for, #1 and #2 could be swapped on the list. This series was iconic. It went all seven games. Each game was a nail-biter. Every hit seemed massively important. And, of course, you cannot mention this series without mentioning game 7. Red Sox manager Gray Little infamously kept his starter, Pedro Martinez, in the game one inning too long, allowing the Yankees to put up 3 runs and tie the game at 5-5 in the bottom of the eighth inning. Naturally, the game couldn’t be decided in just nine innings, so the game went to extras tied at 5 before 3rd baseman Aaron Boone hit a walk-off home run off a Tim Wakefield knuckleball to send the Yankees to the 2003 World Series. If it wasn’t for what happened in 2004, this would easily be number 1 on this list.
#1 2004 ALCS
The 2004 ALCS might be the perfect baseball series (for non-Yankee fans). A matchup between two bitter rivals for a chance to play in the World Series. Two teams that played an iconic, hard-fought, seven-game series the year prior that ended in an extra-innings walkoff home run! The Yankees had added the 2003 AL MVP to their already stacked roster, a player that Boston infamously traded for the same offseason but was denied due to an unprecedented ruling from the MLBPA! However, this is baseball, not a soap opera. Regardless of how interesting the backstory is, the game is played on the field. So how about that game? Well, the Yankees’ offense looked utterly dominant through the first 3 games of the series. They scored 32 total runs in the first three games of the series, winning each of the games as well to take a 3-0 advantage over Boston. The Sox came back to win game 4 in Boston in an extra-innings thriller and did the same thing the next night to make it only a 3-2 series lead. With the series back in New York, Curt Schilling (in his infamous bloody sock game) dominated the Yankees’ offense as the Sox tied the series up 3-3. Game 7 lacked the drama of the 2003 ALCS, but the Red Sox had done the impossible and beat the Yankees to advance to the 2004 World Series after being down 3-0 in the series. It was the series that officially ended the late 90s and early 2000s dominance of the New York Yankees and helped the Red Sox end their long World Series drought. This wasn’t just the best postseason series in Yankees and Red Sox history; it was the best postseason series in MLB history!
The Yankees and Red Sox will add another chapter to their storied history this season. Who do you think will come away victorious? Let me know in the comments below. Thank you for reading and as always stay tuned for new articles coming soon!