Ranking the 10 best Chicago Cubs teams by winning percentage

The Chicago Cubs have existed since the 1870s, when they were known as the Chicago White Stockings, changing their name to the Colts, Orphans, and finally the Cubs in 1904. Although it has not always translated to postseason success, the Cubs have put together their fair share of memorable regular season performances. This list will feature the top ten Cubs seasons by regular season win percentage. 

Note: this list will consider seasons in which the Cubs played at least 150 games. For example, as impressive as the 1876 White Stockings’ 67-17-2 record was, the sample size is too small to be included on this list. As such, the Cubs’ pennant-winning 1918 season, in which the team went 84-45-2 (.651) will receive an honorable mention.

10. 1904 - 93-60-3 (.608) 

The Cubs won 93 games in 1904 which would almost certainly be enough for a playoff berth in today’s game. In 1904, however, there were no playoffs and the top team in each league would automatically win the pennant, advancing to the World Series. The Cubs finished 13 games behind the New York Giants who won the pennant with a 106-47 record.

9. 1945 - 98-56-1 (.636)

The 1945 team featured seven all-stars, including Phil Cavaretta, Stan Hack and Bill Nicholson. Cavaretta also won the batting title with a career-high .355 average. The team won the pennant and advanced to the World Series against the Detroit Tigers. Unfortunately for the Cubs, 1945 was the year Bill Sianis allegedly put the ‘Curse of the Billy Goat’ on the team. The Cubs lost the World Series in seven games and would not win a pennant for another 71 years.

8. 2016 - 103-58-1 (.640)

Speaking of 71 years, the 2016 squad will forever be remembered by Cubs fans as the team that finally broke the ‘Curse’. The team set the record for most wins at Wrigley Field in a single season with 57. 2016 also featured career years from team staples Kris Bryant and Anthony Rizzo, both of whom finished top-five in MVP voting, with Bryant taking home the award. The 3-1 series comeback from Kris Bryant’s game-tying home run in Game 5 to Ben Zobrist’s go-ahead RBI double in Game 7 will go down in history as one of the greatest World Series of all time.

7. 1908 -  99-55-4 (.643)

After winning their first World Series the previous year, the Cubs wasted no time in recapturing their success. Their double-play combo of Joe Tinker, Johnny Evers, and Frank Chance all put up good offensive numbers, with Evers putting up a team-leading 143 OPS+. The real star of the team, however, was the starting pitching, namely that of Mordecai “Three Finger” Brown. Brown pitched to a 29-9 record with nine shutouts and a 1.47 ERA. In the World Series, Brown won Games 1 and  4, leading the Cubs to a five-game World Series win over the Detroit Tigers.

6. 1929 - 98-54-4 (.645)

The 1929 Cubs were an offensive unit. Rogers Hornsby led the charge, slashing .380/.459/.679 along with 39 home runs and 47 doubles. Hack Wilson (.345/.425/.618), Riggs Stephenson (.362/.445/.562), and Kiki Cuyler (.360/.438/.532) also put up great offensive seasons. The Cubs lost the World Series in five games to the Philadelphia Athletics, including an infamous Game 4 loss in which the Cubs blew a seventh-inning eight-run lead after Hack Wilson lost two fly balls in the sun.

5. 1935 - 100-54 (.649)

In 1935, the Cubs continued their trend of winning the pennant every three years (‘29, ‘32, ‘35, ‘38) with another strong offensive team. Catcher Gabby Hartnett won the NL MVP award with a .344 batting average and a 151 OPS+. Stan Hack and Chuck Klein were also solid contributors, and Phil Cavaretta was in his first full season with the club. The team faced the Tigers in the World Series, losing in six games on a Goose Goslin walk-off single.

4. 1910 - 104-50 (.675)

After missing out on the pennant in 1909, the Cubs returned to the top of the heap in 1910. Mordecai Brown was still a dominant pitcher, going 25-14 with a 1.86 ERA. On offense, seven of the starting nine had an OPS+ over 110. The Cubs faced the Philadelphia Athletics in the World Series. Athletics pitcher Jack Coombs pitched back-to-back complete game victories, as the Cubs lost in five games in what would be the last pennant-winning season for player-manager Frank Chance.

3. 1909 - 104-49-2 (.680) 

The Cubs could have easily won four pennants in a row if not for the Pittsburgh Pirates winning 110 games. Star catcher Johnny Kling took a year off from baseball and his replacements put up a combined OPS+ of below 80. As was the story of many early 1900s Cubs teams, the starting pitching, led by Mordecai Brown, carried the team. Brown put up a 1.31 ERA over 342.2 innings, which was the second-lowest ERA of his career. To this day, the 1909 Cubs are tied with the 1942 for the best single-season record to miss the postseason.