I'm a fairly young Yankee fan. I'm not old enough to remember the dynasty of the '90s. I was 7 when Aaron Boone got his middle name in Boston, and I didn't see it - I had gone to sleep in the 6th or 7th inning, fully believing the Red Sox were going to the World Series (fun fact - I didn't believe we won until my dad showed me the newspaper the following morning). In my lifetime, I remember more Red Sox World Series wins than I do Yankees. The point is, there have been a lot of bad moments in the rivalry in my lifetime.
Which brings me to September 28, 2011. Also known as the only time I have ever rooted for the New York Yankees to lose a ballgame. For those of you who need a refresher, the Yankees were playing the Tampa Bay Rays, while the Red Sox were playing the Baltimore Orioles. After blowing a 7 game lead in the month of September by losing 17 of their last 23 games, the Red Sox were tied with the Rays for the Wild Card. The Red Sox, who at one point had a 99.6% chance of making the playoffs, were at risk of missing them completely.
The Yankees very quickly sprung out to a 7-0 lead over the Rays, while the Red Sox took a 3-2 lead over the Orioles. Late in the game, a rain delay struck the Red Sox game, while the Yankees blew the lead in the 8th and 9th innings. The Yankee game went into extras.
In the 9th inning, the Red Sox bullpen blew another lead, leaving their fate in the hands of the Yankees. Would the Yankees prevail and force the Red Sox and Rays to play a Game 163, or would the Rays complete the miracle comeback and take the Wild Card outright? It took only three minutes after the Orioles walked off to find out, when Evan Longoria hammered a pitch by Scott Proctor (remember him?) past the left field foul pole, winning the game and eliminating the Red Sox.