I believe Matt Bradshaw was winning by four points with 10 seconds or so left, and then he got reversed and put to his back when he was a sophomore...however he went on to win two state titles and be superamazing...so I guess it doesn't count as MOST heartbreaking, since he got another chance.

Jhris touched on it earlier, but I won't bring it up now, for I don't want to cry. No amount of consoling from CoachTwink's attractive wife could ease the pain of that one.