Via Montreal Gazette: the site “The Ten Most” has a post on The Ten Most Confusing Road Signs In America
I have personally seen #9 and #4. #4 in St. Paul (the intersection of Montreal Ave, Montreal Ct, and Montreal Way) is by no means the most confusing aspect of St. Paul street naming, which is 7th street, which takes over 8th St and then crosses 6th and the Streets. Surely it would have been easier (and more poetic) to name it Fort Road as it is farther south of downtown.