The Best Chicago Cubs Seasons and Every October Run

By 4Baseball Staff · November 5, 2026 · 11 min read

A guide to the Chicago Cubs' best regular seasons by record and every postseason series in the historical record, from the 1906 team to the 2016 title and the near-misses in between.

The Chicago Cubs have two stories that sit side by side. One is a club that, by the historical record, won more than 11,000 games across 150 seasons and finished above .500 overall (11,419 wins, 10,837 losses, a .513 mark). The other is a club that won the World Series in 1907, 1908 and 2016 and lost it nine other times between 1886 and 1945. Both stories are true, and the gap between them is where most of the Cubs' reputation comes from.

This article walks through the best Cubs seasons by winning percentage and then through every postseason series the club has played, era by era. The records come from the historical record through the 2025 season. Where the database cannot tell us something, such as how a particular game was decided, we say so rather than guess.

The short version: the best Cubs team ever was the 1906 club that won 116 games and lost the Series. The most important was the 2016 club that won 103 and ended a 108-year wait. In between there were pennants in 1910, 1918, 1929, 1932, 1935, 1938 and 1945, then a long stretch with no pennant at all, and then a run of playoff teams that kept running into October walls. For the full franchise story, see the history of the Chicago Cubs; for the people behind the seasons, see the best players in Cubs history.

The best seasons by winning percentage

The historical record ranks Cubs seasons of 100 or more games by winning percentage. The top of that list is not close to modern baseball in style, but it is worth seeing in one place.

The 1885 and 1886 teams were the White Stockings, the Chicago franchise of the 1870s and 1880s that was later renamed the Colts, the Orphans and finally the Cubs (the name has been in use since 1903). Those teams played in a different game, with different pitching distances and a very different postseason, so the sensible comparison is within eras. Within the modern era, the 1906 to 1910 group is the best the club has had.

Two details deserve attention. First, the 1909 Cubs won 104 games and still finished second, which is a reminder that a great record does not guarantee a pennant when another club is better. Second, the 1906 team's 116 wins came in a 154-game schedule, so its .763 winning percentage (116 wins in 152 decisions) is the stronger number than the win total. By the historical record, no later Cubs team has come close to that percentage.

The dynasty of 1906 to 1910

Between 1906 and 1910 the Cubs won four pennants and two World Series, which is the most successful five-year stretch in franchise history. Frank Chance managed the club for most of it; he is the third-longest-serving manager by games in the historical data for the franchise, with 768 wins and 389 losses (a .664 percentage) from 1905 to 1912. The infield of Joe Tinker, Johnny Evers and Chance himself became famous well beyond Chicago, and all three are in the Hall of Fame. The pitching staff was just as important: Mordecai Brown has the lowest earned run average of any Cub with 1,000 or more innings (1.80), and Jack Pfiester (1.85), Orval Overall (1.91) and Ed Reulbach (2.24) are all in the top four.

The postseason results from that era are the most mixed in the sheet:

• 1906: lost the World Series to the Chicago White Sox, two games to four, after a 116-win season. It remains one of the best-known upsets in the sport's history, and it was a city series.
• 1907: beat Detroit four games to none in the World Series.
• 1908: beat Detroit four games to one. This is the title that the 2016 team would end the wait for.
• 1910: lost to the Philadelphia Athletics (today's Athletics franchise) one game to four.

Two things stand out. The Cubs won back-to-back titles in 1907 and 1908 by taking eight of the nine decided games from Detroit (one game in 1907 ended in a tie), a margin that suggests they were clearly the better team. And they lost the 1906 and 1910 Series after seasons of 116 and 104 wins. A short series rewards the better team less often than most fans expect, and these four Series show both sides of it. We take that idea up in why baseball favorites lose so often.

Pennants between the wars: 1918 to 1938

After the dynasty faded, the Cubs won five more pennants in the next three decades and lost the World Series every time. The pattern is stark enough that it shaped the club's identity before the long drought even began.

The 1918 season was shortened by the First World War, which is why the Cubs' 84-45 record covers only 129 games. The 1929 team scored 982 runs, and Rogers Hornsby was the National League's Most Valuable Player that year. It was a high-scoring offense in a high-scoring era, and the Athletics beat it in five games.

The two Yankees series are the most lopsided. In 1932 and 1938 the Cubs were swept four games to none. The 1932 series is remembered for Babe Ruth's alleged "called shot" at Wrigley Field; what happened in that at-bat has been argued for decades, and we will not settle it here. What is not argued is the scoreboard: the Yankees of those years were among the best teams ever assembled, and Chicago had little chance. You can see that other side of the story in the best Yankees seasons and every October run.

The 1935 team is worth a second look. Its 100-54 record is the most wins of the five interwar pennant winners, and Gabby Hartnett was the National League's Most Valuable Player that year. Detroit beat Chicago in six games.

1945, the last pennant for seventy-one years

The 1945 Cubs won 98 games, finished first, and played Detroit in a seven-game World Series. Detroit won four games to three. It was the last World Series the Cubs would play until 2016, a gap of 71 years. Phil Cavarretta was the National League's Most Valuable Player that season.

Fans of a certain kind of history link this series to the legend of the billy goat curse, in which a tavern owner and his goat were said to have been turned away from a game at Wrigley Field. It makes a good story, and many Chicago fans still tell it. We treat it as folklore: the database cannot test it, and a series that went to seven games was decided by baseball events, not by a spell.

What matters for the record is what came after. From 1946 through 1983 the Cubs made the postseason zero times. They lost 103 games in 1962 and again in 1966 (59-103 both years) and had a long run of teams that were not close to contending. The one memorable near-miss of the era was 1969, when the club went 92-70 and finished second in the National League East, behind a New York Mets team that came from far back. There was no wild card at the time, so second place meant no October.

1984 and 1989: division titles and short series

The Cubs returned to the postseason in 1984, 39 years after their last pennant, when they went 96-65 and won the National League East. Ryne Sandberg was the league's Most Valuable Player and Rick Sutcliffe won the Cy Young Award. The National League Championship Series was a best-of-five at the time, and the Cubs lost it to San Diego, two games to three. The historical data records the result but not the order, so we leave the details of the three losses to the box scores.

In 1989 the club won the East again with a 93-69 record. Jerome Walton was the National League Rookie of the Year, and the Cubs faced San Francisco in the National League Championship Series, which they lost one game to four.

These two results are easy to underrate because the Cubs lost. In an era when the league championship series was the only round before the World Series, they are really one-round runs: a division title, then a best-of-five against a team that was at least as good. Short series like these reward whichever team's best pitchers are healthy and on schedule, and the winner is often chosen by a handful of plate appearances. A division title is itself a real accomplishment, and the record shows the Cubs earned two of them in six years.

1998 to 2008: wild cards, a near miss and three first-round exits

The next run was the club's most frustrating in the database. After the 1998 season, in which Sammy Sosa won the National League's Most Valuable Player award and Kerry Wood was Rookie of the Year, the Cubs went 90-73, finished second and won the wild card. They were swept by Atlanta, zero games to three, in the first round.

Then came 2003. The Cubs, managed by Dusty Baker, won the National League Central with an 88-74 record and then beat Atlanta in the division series, three games to two. In the National League Championship Series they faced the Florida Marlins and lost, three games to four. The club led the series three games to one at one point; the sixth game, the fan-interference play in the eighth inning and the loss of the seventh game are the most discussed events of the era, and they remain disputed in the sense that fans still argue about how much any single play mattered. What the record shows is plain: Chicago won three of seven and lost the pennant.

After 2003 the Cubs won division titles in 2007 (85-77) and 2008 (97-64), and both ended in sweeps in the division series. In 2007 they lost to Arizona, zero games to three; in 2008 they lost to the Los Angeles Dodgers, zero games to three. The 2008 team had Geovany Soto as Rookie of the Year and the highest season attendance in the club's historical history (3,300,200). Between them, those two sweeps were six straight postseason losses, which says more about how little a short series forgives than about the 97 wins that came before it.

2015 to 2017: the best three seasons in a century

The turnaround that ended the wait did not arrive as a single great season. It arrived as three. In 2015 the Cubs won 97 games under Joe Maddon, finished third in the division and won a wild-card berth. They beat Pittsburgh in the one-game wild-card round, then beat St. Louis three games to one in the division series. Their run ended when the New York Mets swept them in the National League Championship Series, zero games to four. Jake Arrieta won the Cy Young Award that year and Kris Bryant was Rookie of the Year.

In 2016 the Cubs won 103 games and lost 58, the most wins by a Cubs team since 1910. They beat San Francisco three games to one and the Dodgers four games to two, then played Cleveland in the World Series. Cleveland led the series three games to one. The Cubs won the next three, four games to three overall, to win their first championship since 1908. That was a gap of 108 years, widely described as among the longest title waits in American professional sports. Kris Bryant was the National League's Most Valuable Player.

The 2017 team won the division again, going 92-70. It beat Washington three games to two in the division series, a series that went the distance, and lost to the Dodgers four games to one in the National League Championship Series. The sections below pick up the story from there.

The recent years: 2018 to 2025

The Cubs' record since 2017 is a shorter and quieter story, and the database ends at the 2025 season, so we stop there. In 2018 the club won 95 games and lost the one-game National League wild-card playoff to Colorado. In the shortened 2020 season the Cubs went 34-26, won the National League Central and lost the three-game wild-card round to Miami, zero games to two. In 2025 they went 92-70, finished second and won a wild-card berth. They beat San Diego two games to one in the wild-card round and then lost the division series to Milwaukee, two games to three.

The 2025 series is a fitting last entry. A best-of-five series that goes the distance is the narrowest margin in the format, and Milwaukee, a division rival, won it. Our history of the Milwaukee Brewers covers the club that ended the Cubs' season, and the Cincinnati Reds and Pittsburgh Pirates are the other National League Central clubs the Cubs have shared a division with.

Every Cubs postseason series at a glance

Here is the complete record in the historical record for the modern era, grouped by round.

In the nineteenth century the White Stockings also played the 1885 series against St. Louis, which ended with three wins for each side and is not counted among the club's titles, and lost the 1886 series to the same opponent, two games to four. Those series were organized very differently from the modern World Series, so the table above starts with the modern era.

Common questions

What was the best Cubs team ever? By winning percentage, the 1906 club at 116-36. It lost the World Series to the White Sox. The 1907 team (107-45) won the title and the 2016 team (103-58) ended the long drought, so the answer depends on whether you rank by record or by result.

How long did the Cubs go without a World Series win? From the 1908 title to the 2016 title, 108 years. They did not appear in a World Series at all between 1945 and 2016.

How often did the Cubs lose the World Series after winning the pennant? Between 1906 and 1945 the club won ten pennants and two Series. The eight losses came in 1906, 1910, 1918, 1929, 1932, 1935, 1938 and 1945.

How close was 2003? Close enough to be remembered for it. The Cubs won the division at 88-74, beat Atlanta in the division series and lost the National League Championship Series to Florida in seven games.

Where do the Cubs play, and can I see their live record? At Wrigley Field, which is covered in our ballpark guide. The line at the top of this article shows the club's live record and next game.

Where to go next

Start with the club's team page for the current schedule and the Wrigley Field page for the park's reference data. For the long view, the history of the World Series puts every Cubs appearance in context, and the Cubs topic page collects current news about the club.