The Red Sox and Dodgers only faced off once before in a World Series (1916 when the Dodgers were the Brooklyn Robins), but there's still plenty of history between the two franchises. Let's face it: Milwaukee is a great team, but Red Sox vs Brewers wouldn't have been nearly as appetizing. As much as we all love the underdog (the Brewers have never won a World Series), this is a marquee matchup between two heavyweight, big-market ballclubs that have had countless connections over the years.