The Chicago Cubs have won the World Series three times in their history.

Key Victories

1907 : The Cubs swept the Detroit Tigers 4-0-1, marking their first championship after a record 116-win regular season in 1906 (though they lost that Series). This win kicked off a golden era under manager Frank Chance.

1908 : They repeated as champions, defeating the Tigers again in five games, becoming the first MLB team to win back-to-back titles and play three straight Series. Stars like Mordecai "Three Finger" Brown dominated.

2016 : Ending a 108-year drought —the longest in North American sports—the Cubs beat the Cleveland Indians 4-3 on November 2, clinched by Aroldis Chapman's save after a rain delay pep talk from Jason Heyward. This epic run featured Kris Bryant, Anthony Rizzo, and a cursed goat-breaking narrative fans still celebrate.

World Series Record Overview

Year| Opponent| Result
---|---|---
1906| Chicago White Sox| Lost 2-4
1907| Detroit Tigers| Won 4-0-1
1908| Detroit Tigers| Won 4-1
1910| Philadelphia Athletics| Lost 3-4
1918| Boston Red Sox| Lost 2-4
1929| Philadelphia Athletics| Lost 1-4
1932| New York Yankees| Lost 0-4
1935| Detroit Tigers| Lost 3-4
1938| New York Yankees| Lost 1-4
1945| Detroit Tigers| Lost 3-4
2016| Cleveland Indians| Won 4-3

Why 2016 Stands Out

That 108-year gap fueled legends like the Billy Goat Curse (from 1945) and black cat incidents, turning Cubs fans into eternal optimists. No titles since—recent playoff runs (e.g., 2020 Wild Card) keep hope alive amid rebuilds under Jed Hoyer.

"After a 108-year wait... the Cubs had to wait just a little longer."

TL;DR : Cubs won in 1907, 1908, 2016 —no others.

Information gathered from public forums or data available on the internet and portrayed here.