This fascinates me, more than it probably should: Since the advent of the 162-game schedule, the Boston Red Sox have never won 100 games. Of course, many franchises have failed to achieve that mark, but it's interesting in Boston's case because the Red Sox have long been one of the most successful teams in the majors.
Since 1967, when the Impossible Dream Red Sox snapped a string of eight consecutive losing seasons and won the American League pennant, the Red Sox have the second-most wins in the majors, trailing only their rivals from the Bronx, and have had just nine losing seasons in those 51 completed campaigns.