Here are the Cubs' 5 best regular seasons

February 23rd, 2021

CHICAGO -- There are many ways to define the best season in a team's timeline. Maybe it is the most surprising club to capture World Series glory, or a team that racked up a historic number of wins in the regular season.

For fans, their club's "best season" might be the one that made them fall in love with baseball, or had the best cast of memorable characters. Sometimes -- as is the case with the 1969 Cubs -- fans hold a particular team dear to their collective hearts, even if success did not arrive in the end.

In their 145 years of existence, the Cubs have won more than 11,000 games and tasted champagne after a World Series three times. The 2016 team will go down as one of the most memorable in baseball history, but the 2015, 1998, 1989 and 1984 teams are also revered by Cubs fans. And that's not even getting into the beloved clubs of the 1930s and '60s.

For this examination of Cubs history, however, we'll stick to a more cut-and-dried approach. Here are the five best teams (strictly in terms of regular-season win total) in the long, storied history of the franchise:

1) 1906 -- 116 wins
To find the best Cubs team ever, at least in terms of wins, one has to search all the way back to the pre-Wrigley Field era, when the club couldn't even boast the North Siders moniker because it would've been geographically inaccurate. The 1906 Cubs, who called West Side Park home, won 116 games, which remains tied with the 2001 Mariners for most all-time, yet the Cubs did so in a 154-game schedule, making their .763 win percentage the highest on record (since 1900).

Postseason: Lost to the White Sox (dubbed the "Hitless Wonders" for American League-low .230 team batting average) in six games. The Chicago rivals were tied, 2-2, before the White Sox rattled off 16 runs across the final two wins.

2) 1907 -- 107 wins
Coming off the historic 116-win campaign, the Cubs continued their run of dominance in the National League by surpassing the century mark again. The Pirates were 17 games back in second place. This Cubs team had the famous infield combination of Tinker to Evers to Chance, but was not an offensive powerhouse. No, Chicago soared up the standings behind the strength of its pitching, posting a 1.73 ERA as a team en route to a second straight World Series berth.

Postseason: After Game 1 with the AL-champion Tigers ended in a tie, the Cubs swept the next four games of the Fall Classic. Orval Overall, Ed Reulbach, Mordecai Brown and Jack Pfiester spun a collective 0.75 ERA on the mound.

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3) 1910 -- 104 wins
Another year, another 100-plus wins for the pitching-powerhouse Cubs of the early 20th century. Three Finger Brown (1.86 ERA) and King Cole (1.80 ERA) led a staff that fashioned a 2.51 ERA as a team. This was, however, shaping up as Chicago's last shot at keeping its incredible run atop the NL going. The Cubs won the pennant by 13 games over the New York Giants, but would not capture the league title again until 1918.

Postseason: The Cubs' arms simply could not stop the bats of the Philadelphia Athletics, who took the World Series in five games. Home Run Baker and Eddie Collins helped lead the A's to an .857 OPS in the Series.

4) 1909 -- 104 wins
The Cubs won consecutive World Series championships in 1907-08 and cruised past the 100-win mark again in '09. The problem? Well, those pesky, Honus Wagner-powered Pittsburgh Pirates won 110 games to claim the NL pennant, leaving the Cubs out in the cold in the days before multiple divisions. Mordecai Brown was particularly brilliant in '09, winning 27 games, fashioning a 1.31 ERA and logging 32 complete games in 50 appearances (342 2/3 innings).

Postseason: Did not qualify.

5) 2016 -- 103 wins
This Cubs team will go down as not only one of the great teams in franchise lore, but one of the more notable squads in baseball history. After years of rebuilding, the North Siders emerged as true contenders in 2015 and then capitalized on that momentum one year later. Kris Bryant took home the NL MVP Award, Kyle Hendricks (2.13) claimed an ERA title, Jon Lester (19-5, 2.44) was the runner-up for the NL Cy Young Award and this group of young, talented stars etched their name in the history books.

Postseason: In one of the great World Series of all-time, Chicago defeated Cleveland in seven games. Both teams had historic droughts (Chicago hadn't won since 1908 and Cleveland since 1948). So, naturally, it took a 10th inning for the Cubs to pull off their dramatic, 8-7, win to erase the 108-year championship cold spell.