NL Pennants

Verified Timeline

Lore & Background

Throughout the club's history, the Cubs have played in a total of 11 World Series. The 1906 Cubs won 116 games, finishing 116–36 and posting a modern-era record winning percentage of .763, before losing the World Series to the Chicago White Sox by four games to two. The Cubs won back-to-back World Series championships in 1907 and 1908, becoming the first major league team to play in three consecutive World Series, and the first to win it twice. Most recently, the Cubs won the 2016 National League Championship Series and 2016 World Series, which ended a 71-year National League pennant drought and a 108-year World Series championship drought, both of which are record droughts in Major League Baseball. The 108-year drought was also the longest such occurrence in all major professional sports leagues in the United States and Canada. Since the start of divisional play in 1969, the Cubs have appeared in the postseason 11 times through the 2024 season.

In Their Own Story

The narrative of the Cubs' pennants is defined by specific eras and a notable drought. In 1885, the White Stockings played the St. Louis Browns in a disputed series that ended in a tie, splitting a $1000 prize. The rematch in 1886 saw Chicago lose to the Browns, who claimed victory after a controversial slide by Curt Welch. Moving into the modern era, the team's dominance peaked with three consecutive pennants from 1906 to 1908. While they won World Series titles during this time, their championship run halted in 1908. The source highlights that the Cubs' next pennant win did not occur until 2016, ending a period where they had not secured the title since 1945. This 71-year gap between 1945 and 2016 stands as the longest drought in their recent history.

Reader's Guide

The Cubs are known as 'the North Siders', a reference to the location of Wrigley Field within the city of Chicago, and in contrast to the White Sox, whose home field (Rate Field) is located on the South Side. Through 2024, the franchise has played the most games in MLB history, with an all-time regular season record of 11,419–10,837–161 (.513).

Did You Know?

• The Cubs were first known as the White Stockings and were founded in 1870.
• The Cubs have played in a total of 11 World Series through their history.
• The 1906 Cubs set a modern-era record winning percentage of .763.
• The Cubs won back-to-back World Series in 1907 and 1908.
• The Cubs' 108-year World Series drought is the longest in North American professional sports history.