Who has the most playoff points in their career against each of the following teams?
Boston Bruins?
Chicago Black Hawks?
Detroit Red Wings?
Montreal Canadiens?
New York Rangers?
Toronto Maple Leafs?
I only guessed one of those six correctly myself before looking it up.
I'll make 2 guesses each. If you'll only accept one, go with the first. Guessing by teams who played them multiple times in eras while the opponents were successful (Edmonton vs Boston in the 80s, Boston vs Toronto in the 70s, etc)
Boston Bruins? Gretzky? Messier?
Chicago Black Hawks? Howe? Delvecchio?
Detroit Red Wings? Frank Mahovlich? Rocket Richard?
Montreal Canadiens? Stastny? Goulet?
New York Rangers? Bossy? Trottier?
Toronto Maple Leafs? Orr? Espo?
I'm sure at least one of them is someone I would never think of, so I'm not overly confident, but maybe I found a bullseye here.