You think you know baseball history, but the last two decades have basically been a fever dream for anyone who likes "predictable" sports. Honestly, if you told a fan in 2005 that the Chicago Cubs would break a century-long curse, or that a team from Texas would win it all by spending half a billion dollars on two guys, they’d probably tell you to go home.
The list of past 20 world series winners isn't just a record of who was the best. It’s a record of who survived. It's a mix of "god squads" buying their way to glory and scrappy underdogs who barely crawled into the postseason with 83 wins.
Let's get into what actually happened.
The Most Recent Drama: Back-to-Back Blue
Winning once is hard. Winning twice in a row in the modern era is supposed to be impossible. Before the Los Angeles Dodgers pulled it off in 2024 and 2025, we hadn't seen a repeat champion since the 2000 Yankees.
The 2025 World Series was a weird one. You had the Dodgers facing the Toronto Blue Jays, the first time the Fall Classic went north of the border since the early 90s. It went the full seven games. Yoshinobu Yamamoto basically cemented his legend in Game 7, pitching the Dodgers to a 5-4 victory in the 11th inning.
But 2024? That was the "God Squad" year.
Everyone talks about the Ohtani effect, but Freddie Freeman was the one who actually broke the New York Yankees' hearts. His walk-off grand slam in Game 1 of the 2024 series is already being called one of the most iconic moments in the history of the sport. It sort of took the air out of the Bronx before the series even really started.
The Recent Honor Roll (2020-2025)
- 2025: Los Angeles Dodgers (def. Toronto Blue Jays, 4-3)
- 2024: Los Angeles Dodgers (def. New York Yankees, 4-1)
- 2023: Texas Rangers (def. Arizona Diamondbacks, 4-1)
- 2022: Houston Astros (def. Philadelphia Phillies, 4-2)
- 2021: Atlanta Braves (def. Houston Astros, 4-2)
- 2020: Los Angeles Dodgers (def. Tampa Bay Rays, 4-2)
The 2023 Texas Rangers victory is actually pretty fascinating because they missed the playoffs entirely the year before. They basically went from "who are these guys?" to World Champions because they signed Marcus Semien and Corey Seager to massive contracts. It was a business plan that actually worked, which is rare.
The Mid-2010s: Curses and Even Years
If you want to talk about the past 20 world series winners, you have to talk about the San Francisco Giants and the Chicago Cubs.
The Giants had this "Even Year Magic" thing going on. 2010, 2012, 2014. They weren't always the best team on paper, but Madison Bumgarner in 2014 was a literal cheat code. He came out of the bullpen in Game 7 against Kansas City and just refused to give up a run. It was legendary.
Then came 2016.
The 2016 World Series is arguably the greatest baseball series ever played. The Cubs were down 3-1 against Cleveland. They forced a Game 7. There was a rain delay. Jason Heyward gave a speech in a weight room. Ben Zobrist hit a double. The 108-year drought ended. Honestly, it’s still hard to believe it happened.
A Decade of Variety (2010-2019)
- 2019: Washington Nationals (A total Cinderella story—they were 19-31 in May)
- 2018: Boston Red Sox (Total dominance, 108 regular season wins)
- 2017: Houston Astros (Controversial, sure, but they beat the Dodgers in 7)
- 2016: Chicago Cubs (The curse-breaker)
- 2015: Kansas City Royals (The ultimate "contact hitters" team)
- 2014: San Francisco Giants (The Bumgarner Show)
- 2013: Boston Red Sox (The "Boston Strong" year)
- 2012: San Francisco Giants (Swept the Tigers)
- 2011: St. Louis Cardinals (David Freese’s Game 6 is still a miracle)
- 2010: San Francisco Giants (The start of the dynasty)
The 2011 Cardinals are the biggest outlier here. They were 10.5 games out of a playoff spot in late August. They shouldn't have been there. David Freese was down to his last strike—twice—in Game 6. If you're looking for proof that baseball is chaotic, that's your evidence.
The Forgotten Era: 2006 to 2009
The start of this 20-year window was dominated by the NL East and the "Red October" of Philadelphia.
In 2008, the Phillies beat the Tampa Bay Rays in a series that was literally paused by rain for two days in the middle of a game. It was messy. But it gave Philly their first title since 1980.
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The 2006 St. Louis Cardinals are actually the "worst" team to ever win a World Series if you look at regular season stats. They won only 83 games. They barely finished above .500. Yet, they handled a 95-win Detroit Tigers team in just five games. It sort of proves that the regular season is just a suggestion once October hits.
The Foundation Years
- 2009: New York Yankees (The last of the Jeter-era rings)
- 2008: Philadelphia Phillies (Cole Hamels was untouchable)
- 2007: Boston Red Sox (Swept the Rockies)
- 2006: St. Louis Cardinals (The 83-win wonders)
Why the "Best" Team Usually Loses
Looking at the past 20 world series winners, the team with the best regular season record has only won the whole thing about 25% of the time.
Why?
Postseason baseball is a different sport. It’s about having two elite starters and a bullpen that can throw 99 mph for three innings straight. The 2019 Nationals had Strasburg and Scherzer. The 2014 Giants had Bumgarner. The 2024/2025 Dodgers had... well, they had a billion dollars and a lot of depth.
A huge misconception is that you need a lineup of All-Stars. You don't. You need a "hot" hitter. Think about Jorge Soler for the Braves in 2021 or David Freese in 2011. These aren't always the guys you'd pick for your fantasy team, but they became gods for two weeks in October.
How to Use This Info
If you're betting or just trying to sound smart at a bar, stop looking at win-loss records from June.
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Look at Bullpen ERA in September. Look at starting pitcher health. The teams that won over the last 20 years were almost always the ones that got their injured aces back just in time for the Division Series.
Also, keep an eye on the "Wild Card" teams. Since the format expanded, the "underdog" has a massive psychological advantage. They've been playing "must-win" games for a month while the division leaders have been coasting.
The Dodgers might be the current kings, but history shows that a repeat is nearly impossible and a collapse is always one "rain delay" or "dropped fly ball" away.
Check out the official MLB history archives for the box scores of these games—some of the pitching performances, like Cliff Lee in 2009 or Josh Beckett in 2003 (just outside our window), are masterclasses in how to handle pressure.
Study the 2011 Game 6 or the 2016 Game 7 specifically. Those two games contain every lesson you need to know about why this sport is so maddeningly beautiful.
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Keep an eye on the trade deadline this coming July. Usually, the team that wins the World Series is the one that trades for a middle-relief pitcher nobody has heard of, who then goes on to throw six scoreless innings in the playoffs. That's the real secret.