1999 ALCS: Yankees over Red Sox, 4-1
Despite the storied history of both franchises, the Red Sox and Yankees met for the first time in the playoffs in 1999, four years after the implementation of the wild card. Like all of the previous playoff appearances for the Red Sox since 1919, this one didn’t end very well. Pedro Martinez (left) provided the bright spot for the Sox, striking out 12 Yankees in seven innings in what was supposed to be a duel with Roger Clemens. But Pedro provided the only win for the Red Sox in that series as the Yankees advanced, 4-1.