Best Quarter Century MLB Team: Boston Red Sox
This iconic, legendary team knows a thing or two about winning championships

There have been some outstanding moments that happened in Major League Baseball over the last 25 years. So, who is my pick of the best MLB team that made the biggest impression since the year 2000? They are none other than the Boston Red Sox. Why? It's because they had some of the best players we enjoyed seeing over that span. Players such as David Ortíz, Pedro Martínez, Dustin Pedroia, Jason Varitek, Josh Beckett, and the late Tim Wakefield. The Red Sox won four World Series titles in a span of 15 years (2004, 2007, 2013, 2018). The Red Sox-Yankees rivalry dates back to 1919, when legendary Yankees player Babe Ruth was traded to the Red Sox. Around this time started one of baseball's most well-known superstitions: The Curse of the Bambino. The Red Sox didn't have a World Series title for the next 86 years until 2004.
As of 2025, the overall record between these two teams in the regular season is 1,249-1,037, favoring the Yankees, a Postseason record of 14-13, again in favor of the Yankees, and the all-time series record of 1,263-1,050, once again in favor of, you guessed it, the Yankees. Both teams have met a total of 2,327 times. In case you're curious when they'll face each other next season, it'll start on April 26, 2026. The rivalry is not as hyped up as it was back in the 2000s, but whenever these two teams face each other, expect it to be intense. Fans of both respective teams still support them and engage in lots of trash talking.
Speaking of 2004...
The Comeback Kids and Achieving the Impossible
In the 2004 American League Championship Series (ALCS), they played against the then Anaheim Angels (now Los Angeles Angels). Down three games to none, the Red Sox were desperate to stay alive in the ALCS and trying to save their season. To everyone's surprise, they not only came back and won the American League pennant, but they accomplished something that hasn't been done in MLB before: becoming the only team in the league to come back from a 3-0 deficit to win a best-of-seven series, a stat that still holds to this day. David Ortíz was named ALCS MVP.
Their final opponent was the St. Louis Cardinals in the World Series, where they swept them in four games. This was Boston's first World Series title in 86 years, officially breaking the so-called Curse of the Bambino. Manny Ramírez was named World Series MVP. Their historic win came eight months after the New England Patriots won Super Bowl XXXVIII. This was the first time Boston had a World Series and Super Bowl championship in the same year. The 2004 World Series had nearly 26 million viewers, ranking it among the best Fall Classics of all time. I included the aforementioned World Series on my list of my favorite World Series games of the last 25 years in a story I wrote several months ago, which you can read at the end of this story. During the 2024 regular season, the team honored Tim Wakefield, who passed away in October 2023 after a battle with cancer at the age of 57. The following season, they celebrated the 20th anniversary of their history making championship and also in that same year, three former Red Sox players were inducted into the Red Sox Hall of Fame. Two of them included Dustin Pedroia and Jonathan Papelbon.
Let's get the conversation started in the comments section below. What are some of your favorite Boston Red Sox moments of the last quarter century? Who is your favorite and least favorite Red Sox manager? Who are some of your favorite Red Sox players that you enjoyed seeing the most and which ones you've heard of, but don't hear anyone talk about these days? If you enjoyed this story, please give it a like. Make sure you follow me on my socials. Finally, like this story and please leave a generous one-off tip. It'll be found at the end of this story. Big or small, your tips will support creators like me so we can keep publishing new stories and share them with everyone.
About the Creator
Mark Wesley Pritchard
You can call me Wesley. Former cosplayer, retro gaming fanatic, die-hard Texas Rangers fan, and nostalgic freak. Need I say more?
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