The Chicago National League franchise was known as the White Stockings, Colts, and the Orphans before settling in as the Cubs in 1903. They won the very first NL pennant in 1876, and under Cap Anson they won five NL titles in the 1880s. In the first decade of the 20th century the Cubs were the best team in baseball, winning a record 116 games in 1906, 107 games in 1907, 99 games in 1908, and 104 games in 1909 and 1910. In four of those seasons the Cubs won NL pennants, garnering World Titles in 1907 and 1908. Cub faithful are still waiting for their next World Championship.

Mainstays on that team were Three-Finger Brown, Ed Reulbach, Frank Chance, Johnny Evers, Joe Tinker, Frank Schulte, and Jimmy Sheckard. Under the guidance of first baseman Chance, they continued to contend well into the Teen's.

In 1918 a younger team, built around pitchers Hippo Vaughn, Lefty Tyler, and Claude Hendrix, grabbed the NL flag but were beaten in the series by the Babe Ruth-led Red Sox. The 1920s saw six different managers for the Cubs, and not surprisingly they produced mixed results. But in 1929, due in large part to newly acquired Rogers Hornsby, the Cubs won the pennant with 98 victories. It was the first of four pennants that occurred in three year intervals (1929, 1932, 1935, 1938). In all four cases the Cubs lost the World Series. Hack Wilson, Kiki Cuyler, Charlie Grimm, Billy Herman, Gabby Hartnett, Stan Hack, Billy Jurges, Phil Cavarretta, Riggs Stephenson, Lon Warneke, and Bill Lee formed the core of those pennant winning Cubs ball clubs.

By 1945 Grimm was managing the team and Chicago won a tight race for the flag over the favored Cardinals. Their loss in the 7th game of that World Series is the franchise's last appearance in the Fall Classic. After a 3rd place finish in 1946, the Cubs finished in 5th place or lower for the next twenty seasons. Only the great performance of Ernie Banks gave Cub fans any reason to smile during those years. By 1969 Leo Durocher managed a talented Cub team with players like Ron Santo, Billy Williams, Ferguson Jenkins, Don Kessinger, Banks, Ken Holtzman, and Randy Hundley. But the Miracle Mets lapped the Cubs and won the NL East and the pennant. The Cubs have rarely been so close to the Series since.

The 1970's brought continued disappointment despite the efforts of Bill Madlock, Manny Trillo, Rick Reuschel, Bill Buckner, and Dave Kingman. In the 1980s the Cubs slowly gathered a group of players that exploded in 1984 to win 96 games - a 25 game improvement over the previous year. Favored to win the pennant, the Cubbies stuck to their losing form and squandered a 2-0 lead against the Padres in the NLCS. Once again they failed to end their World Series drought. The best player on the Cubs in the 1980s was Ryne Sandberg, the slugging second baseman. He won the 1984 MVP award and plugged the middle infield spot for Chicago for 15 seasons. Andre Dawson added fire to the Cub attack in the late 1980s and the team won a division title in 1989, only to succumb to the Giants.

The next eight years brought seven losing seasons, before the team revived in 1998 to win a wildcard spot in the playoffs. They quickly exited - leaving Sammy Sosa's home run accomplishments and the play of Mark Grace as the best things to happen to the franchise in the decade.

In 2004 the Chicago Cubs finished 3rd in the Natioanl League Central Division with a 89-73 record.

In 2006 the Chicago Cubs finished with a 66-96 record, last place in their division, and 3rd worst record in baseball.