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Old Grumbly Fan’s Red Sox Playoff Preview

By John Keough | September 30, 2025
Last Updated: September 30, 2025
Editor's Note: This piece appears in our Columns section and includes commentary and/or analysis
The views expressed in this article do not represent the views of This Week in Worcester

Well, here we are again. Red Sox-Yankees!

Let’s rehash the numbers: The Red Sox and the Yankees have played in the ‘official’ playoffs 5 times.

1999 ALCS Yankees 4 Red Sox 1

This series was the end of the three championships in 4 years run for the Yankees. The lone win for the Sox was a 16-1 blowout that featured a shutout from Peak Pedro.

2003 ALCS Yankes 4 Red Sox 3

This was the Cowboy Up Red Sox team, and this series featured the brawl with Pedro throwing a charging Don Zimmer to the ground in Game 3. It ended with Aaron Boone homering off of Tim Wakefield, and set the scene for the greatest season in baseball history.

2004 ALCS Red Sox 4 Yankees 3

You have read all the books and have seen all the documentaries. By the way, I do not care at all, in any way, about Matt Damon’s opinion about the 2004 Red Sox. He’s from Cambridge. Get me a 75-year-old deli owner, and let him tell me how he feels.

This was the best series ever, and the World Series after it felt like an exhibition series. Eat it Yankee fans.

2018 ALDS Red Sox 3 Yankees 1

This Red Sox team was absolutely loaded. It still hurts to see Mookie Betts playing for the Dodgers.

2021 Wild Card Game Red Sox Win 6-2

This was the last game in the playoffs between the storied franchises. This was at the beginning really of Aaron Judge’s rise to be one of the few superstars in baseball.

Bonus ROUND

1978 Play in, Technically a regular season game under the old rules. Yankees won 5-4 on Bucky f***in Dent’s 3-run homer.

Both teams have won 12 games in the playoffs against the other. The Red Sox have lead in playoff series wins with three wins to the Yankees two.

The Red Sox also have a 9-4 record against the Yankees this year, and a 5-2 record in the Bronx, where all three of the games in this series, if needed, will take place

Two lefties will start Game One with the Red Sox putting their ace on the mound, , Garrett Crochet, against Yankee All-Star Max Fried.

Crochet was 18-5 with a 2.59 ERA and 255 strikeouts during the regular season and is likely to finish in the top two for the American League Cy Young Award this year.

Fried was 19-5 with a 2.86 ERA and 189 strikeouts. He had one of the best run-support records in all of baseball this year.

Tonight should be a low scoring game. For the Red Sox, game one is a must-win to get momentum and get into the Yankees’ heads.

My prediction?

Red Sox Sweep! 2-0

Game 1 Sox 3 Yankees 1

Game 2 Sox 5 Yankees 4

Aroldis Chapman gets the save in both.

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