The 16th of October is a historic day in Boston Red Sox history.

Not the good kind of historic, however.

It was 2003 and the Sox still found themselves hampered by the Curse of the Bambino 85 years after the infamous Babe Ruth trade. And entering Game 7 of the American League Championship Series, Boston was closer than ever to breaking the dreaded curse.

Unfortunately, things didn’t end up swinging in Boston’s favor. (Not that year, at least.)

With the score tied heading into extra innings, the Red Sox brought out Tim Wakefield to try and finish off the Yankees. But the knuckleballer couldn’t get around Aaron Boone in the 11th, allowing the then-30-year-old to wrap a walk-off solo shot around the foul pole at Yankee Stadium.

And the rest, they say, is history.

(If you’re having trouble watching the video above, click here.)

At least the Sox managed to break the curse the following year. But boy, was this a bitter moment in Boston sports history.

Thumbnail photo via Jeff Curry/USA TODAY Sports Images