I MAY be all wet here, but something tells me I am not. Cribbage is a game played on a board that has (usually) two rows of 30 holes each that you must traverse twice, for a total of 121 points, in order to win the game. Some boards have two sets of 30 holes up and two back to the home peghole.
Each row of thirty holes is called a street, and it is very common when playing cribbage to say of an awesome performance that "I was two streets ahead of him by the last hand." That is RARE!!! When you lose by 31 points to 60 points, that's called a skunk. When you lose by more than 60 points (two streets), it's called a double skunk, and I've only suffered that once in almost half a century of cribbage playing.
My swag is that being streets ahead comes from cribbage.