The 1908 Chicago Cubs season was the 37th season of the Chicago Cubs franchise, the 33rd in the National League, and the 16th at West Side Park. It involved the Cubs winning their third consecutive National League pennant, as well as the World Series for the second consecutive year. This team included four future Hall of Famers: manager / first baseman Frank Chance, second baseman Johnny Evers, shortstop Joe Tinker, and pitcher Mordecai Brown. In 1908, Brown finished second in the NL in wins and earned run average. This would be the last World Series victory for the Cubs until 2016.

The 1908 World Series was the championship series in Major League Baseball for the 1908 season. The fifth edition of the World Series, it matched the defending National League champion Chicago Cubs against the American League champion Detroit Tigers in a rematch of the 1907 Series. In this first-ever rematch of this young event, the Cubs won in five games for their second straight World Series title.