The Stanley Cup is the oldest trophy in North American pro sports, having been first awarded in 1893. It’s been won by many teams both professional and amateur, first as a challenge trophy and later as the league title for organizations like the PCHA, NHA, and eventually the NHL.
All NHL fans know how many times their favorite team has captured the Cup, and chances are they’ll recite the number instantly. The Canadiens have won a league-leading 24. The Leafs and Red Wings are next, followed mostly by fellow Original Six teams, with more recent franchises like the Oilers, Islanders, and Devils having also won several.