The Calder Cup is a tournament of ugly girls who battle in grueling matchups to determine who is the best (hottest) of the worst (ugly girls). It is often used to establish where someone's questionable girlfriend is on the "looks hierarchy". It only applies to girls who are a 5 or less on the 1-10 scale and a girl's echelon is determined using a playoff exit scale (1st round, conference semi-finals, east/west coast finals, or calder cup final).
Because of her hideous, scary face and average body, Billy's girlfriend would exit the Calder Cup playoffs in the East Coast Finals.
by Hershey Bears December 18, 2010