With 4 games left in the 2012 season, the Cubs record is 59-99. Should they lose one more game it will be the first season they lost 100+ games since 1966 when they went 59-103.
103 by the 1962 and 1966 Cubs.
Through the 2008 season, that was the 2003 Atlanta Braves who lost in the NLDS to the Cubs, 3 games to 2.
In 1945. The Cubs lost to the Detroit Tigers in seven games.
season 6 is the last season of lost
89
1945 against the Tigers they lost, Of Course
Through the 2009 season, 21 games by the 1988 Baltimore Orioles. And the Chicago Cubs lost 14 games to start the 1997 season.
As of 2011, the last time the Chicago Cubs played in the world series was in 1945. They played the Detroit Tigers and lost 4 games to 3.
The Cubs went 100-54 in 1935 and won the National League pennant. They lost the World Series to the Detroit Tigers 4 games to 2.
Their first season. 1906.
Prior to the 2010 season when the Longhorns lost 5 out of 6, that was 1997 when they lost 5 out of the final 6 games of the season and wound up with a 4-7 record.
The Cleveland Indians prior to their World Series appearance in 2016 against the Chicago Cubs in which they had lost against the Cubs in seven games the last time they had played in the World Series was in 1997 in which they had played the Florida Marlins and lost to them in seven games. They had also lost in the 1995 World Series to the Atlanta Braves.