I like that you go back to 1927 (versus the featured quiz that starts with the expansion era in 1968). The years before 1968 aren't automatically given, since neither the Ottawa Senators nor Montreal Maroons were considered "Original Six", nor have they won any Cups since 1967. I completed the quiz with 6:25 remaining, so it could definitely be a LOT shorter. It's also annoying to have to type the city as well as the team name. Considering losing the city and reduce the time to maybe 4 minutes, seeing as how you can clear huge sections of the list quickly without the yellow box from the featured quiz.
I just noticed something. I don't understand how there are different percentages for the same team in different years. Did this used to be a yellow box quiz, and it changed without resetting the stats?