9. New York Yankees
Yanks blow 3-0 ALCS lead vs. Boston Red Sox – 2004
A shining moment for Red Sox Nation and a time to forget for Yankee fans, the Red Sox stormed back from a 3-0 deficit in the 2004 ALCS to advance to the World Series, in which they swept the Cardinals to break the Curse of the Bambino after 86 years. As it turned out, Games 4 and 5 were the tough wins for Boston. In the fourth, the Yanks took a 4-3 lead into the bottom of the ninth, when Kevin Millar led off with a walk.
The speedy Dave Roberts was sent in to pinch run, successfully stealing second base before getting knocked home on a Bill Mueller single to send the game into extras. David Ortiz ended the game on a walk-off two-run homer in the twelfth.
The New York bullpen failed again in Game 5, blowing a 4-2 lead by allowing two eighth inning runs. Ortiz again provided the heroics with a game-winning single in the fourteenth inning, ending one of the longest postseason games ever. Surprisingly, the Yanks went down more quietly when the series shifted back to the Bronx for the final two games, losing them 4-2 and 10-3 respectively. The Yankees remain the only MLB team to let a 3-0 lead slip away in a best-of-seven series.
10. Matt Holliday
OF loses fly ball into the gut… or below - Game 2 of 2009 NLDS (St. Louis Cardinals vs. Los Angeles Dodgers)
In a Division Series that ended in a quick Dodgers sweep, Cardinals fans will still blame left fielder Matt Holliday for turning the tide with his ninth inning error in Game 2. The Cards seemed poised to tie the series, holding onto to a 2-1 lead with the Dodgers down to their last out.
With no one on, James Loney hit a fly ball on a line toward Holliday, who lost the ball in the lights. The story goes that the fly ball hit Holliday in the gut, but upon video review, it may have, unfortunately, hit lower than that. Regardless, Loney made it to second on the play, which was followed up with a walk and a game-tying RBI single by Ronnie Belliard. After another walk to load the bases, Mark Loretta hit a walk-off single to give LA a 2-0 series lead.