Red Sox vs. Yankees playoff history: Boston holds October edge

The Red Sox and Yankees are set to add another chapter to their storied rivalry this week when they clash in a best-of-three Wild-Card series at Yankee Stadium.

Boston and New York’s animosity has been in place for over a century as two of the top franchises in MLB.

But for all of their battles over the decades, they’ve actually only met six times in the postseason — not counting play-in games such as Bucky [redacted] Dent’s heroics for New York in 1978. 

History has been on Boston’s side as of late, with the Red Sox having won three straight series against their top rival — and eight of their last nine postseason games in October. 

As the Sox and Bronx Bombers brace themselves for another collision course, here’s a look at the postseason history between both teams. 

1999 ALCS: Yankees win, 4-1

Boston’s efforts to try and halt New York’s late-90s dynasty ended up being in vain, as the Yankees handled their rival in five games en route to a third World Series championship in four years. 

The Yankees set the tone in Game 1 after Bernie Williams hit a walk-off home run in the Bronx, with a lopsided 16-1 win for Boston in Game 3 (featuring a shutout start from Pedro Martinez) standing as the lone blip for New York.

Despite New York advancing by way of a “gentleman’s sweep,” the Yankees only outscored Boston by two runs over the span of the five-game series. 

2003 ALCS: Yankees win, 4-3

An anticipated bout between these clubs with a trip to the World Series on the line, this seven-game showdown further raised the temperature on an already heated rivalry. 

As both teams traded wins in a back-and-forth matchup, tensions exploded in a wild Game 3 at Fenway Park — culminating in a brawl between both clubs where Pedro Martinez tossed Yankees bench coach Don Zimmer to the ground after both benches cleared.

Be it Roger Clemens and Manny Ramirez barking at each other before the scrap or Martinez beefing with both Karim Garcia and Jorge Posada, there was no shortage of drama in this series.

Unfortunately, it was the Yankees who got the last laugh in Game 7 at Yankee Stadium.

Despite Boston holding a 5-2 lead in the eighth inning, Grady Little made the infamous decision to keep a gassed Martinez in the game after throwing over 120 pitches — leading to New York knotting the game up via a three-run rally.

The game carried over into the bottom of the 11th, with Aaron Boone completing the comeback for New York with a solo shot off Tim Wakefield to clinch the pennant. 

It was a crushing result for the “Cowboy Up” Red Sox — and further validation that Boston was seemingly cursed to a fate of disheartening defeats when the calendar flipped to October.

2004 ALCS: Red Sox win, 4-3

One of the greatest series in baseball history, the Red Sox finally exorcised their demons — both for the 2003 ALCS and for the looming “Curse of the Bambino” — with a seemingly improbable comeback. 

The Red Sox became the only team in baseball history to overcome an 0-3 series deficit en route to a series victory — winning four straight against their reviled foe to punch their ticket to the World Series for the first time since 1986. 

Staring at a franchise-crushing four-game sweep at Fenway Park, the Red Sox seized new life in the ninth inning of Game 4 — with a fateful steal of second base from Dave Roberts and subsequent game-tying single from Bill Mueller knotting the game up at 4-4. 

David Ortiz kept Boston’s season alive with a two-run homer in the bottom of the 12th inning, before forcing the series back to New York in Game 5 with a walk-off single in the bottom of the 14th. 

Boston forced a decisive Game 7 after Curt Schilling (7 IP, 4 H, 1 ER) gutted his way to a victory on a surgically repaired right ankle, while the floodgates opened in Game 7 — with Boston and Johnny Damon (two home runs, 6 RBI) completing the comeback with a 10-3 victory. 

David Ortiz took home ALCS MVP honors after batting .387 with three home runs and a whopping 1.199 OPS. 

Just a week later, the Red Sox won their first World Series title since 1918. 

2018 ALDS: Red Sox win, 3-1

After a dominant 108-win season, the 2018 Red Sox charted a path to another World Series title by besting New York, 3-1, in a best-of-five ALDS.

After splitting the first two games at Fenway Park, Boston put New York in a stranglehold in the Bronx — winning the final two games to send the Yankees packing. 

Boston all but delivered the knockout punch in Game 3, beating the Yankees, 16-1, in a laugher. It was the most runs the Red Sox have scored in a preseason game in franchise history, with Brock Holt leading the charge by hitting for the cycle in that win. 

Holt was the first player in MLB history to hit for the cycle in a playoff game. 

2021 Wild Card Game: Red Sox win, 6-2

The last time the Red Sox and Yankees met in the playoffs, it was the final year of MLB’s old Wild Card series format — with one winner-take-all matchup between Wild Card clubs instead of a pair of best-of-three matchups in both leagues. 

Boston and New York had identical 92-70 records, but the Red Sox held the game at Fenway Park as a result of winning the season series, 10-9. An already raucous Fenway Park was further electrified after Jerry Remy — making his final appearance at Boston’s ballpark — threw out the first pitch.

Boston pounced on Yankees starter Gerrit Cole early — with Xander Bogaerts hitting a two-run shot out to center in the first inning before Kyle Schwarber went yard with a solo blast in the third.

Cole didn’t record an out in the third before getting pulled, while Nathan Eovaldi gave up run one earned run and struck out eight over 5.1 innings of work. 

Boston closed out the win, 6-2 — setting the stage for an unexpected playoff run that went all the way to the ALCS. 

 

Conor Ryan is a staff writer covering the Bruins, Celtics, Patriots, and Red Sox for Boston.com, a role he has held since 2023.