What loss other than Iowa hurt you the most?

2003 Cubs loss to Marlins. Still getting over it. I wrote an email to some friends just before the Bartman play (just using as a reference, not an excuse) saying the Cubs were going to do it. My friends still reference this and (properly) blame me. Game 7 looked good when Wood hit his HR, then the roof fell in (again). Now, I am going to cry myself to sleep.

Game 6 sucked, but you have to remember that Game 6 doesn't happen if the Cubs win game 1.
 
Very true about Game 1. Being a Cubs fan, you know at least one game a series will be like that. I was thinking we had gotten that game out of the way in this series instead of waiting until the end of the series like 1984 (Leon Durham). At least we were in the 8th inning in Game 6 in 2003 (OK, I am going to stop now - it still hurts too much).
 
Especially after the officials missed a Jerry Rice fumble on the 49ers final drive.

the only good part about this thread is laughing at Fudge Packer, Viqueen, & Cowgirl fans wallowing in their worst memories ... otherwsie, thanks for making me sad :(
 
Like many others have said: By far it is Game 6 of the 2003 NLCS. Up 3-0 going into the 8th, and allow 8 runs in the 8th? Are you serious? Everyone blames Steve Bartman, and yes it was bad luck, but many people forget that Alex Gonzalez basically blew the game for Chicago with his errors. Cubs easily should have made it to the world series that year. I'm still upset about that game. The way things go for the Cubs, im not sure they will ever get back to the NLCS again.
 
Any sport, any year, any other team besides Iowa.

I have to go with Drake losing in the NCAA tournament to Western Kentucky. Heartbreaking.

What? That was awesome! Finally after an entire year of having to hear about Drake the frauds were exposed! Not at the time but after losing game 7 the Bartman game for the Cubs that was our year...
 
The 1998 Class 1A final. Rock Valley beating IMS. IMS would have finished the season 29-0 if they could have kept up with the height of Rock Valley.

The Bartman Game.
 
The 1988 substate basketball finals. Pleasant Valley beats Hempstead by 3. Ugh.

Also the 1996 Superbowl. The only blemish on the Steelers dynasty. Thank you, Neil O'Donnell.

EDIT: And the 1995 AFC Championship game (San Diego vs. Pittsburgh). Thank you ISU grad Dennis Gibson for tipping away the game-winning TD pass in the endzone.
 
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The 1996 World Series, the Braves take the first 2 at Yankee Stadium then proceed to lose the next 4. A close runner-up would be the 91 series between the Braves and Twins, I still hate Kent Hrbek to this day for pulling Ron Gant off first base in game 6 that the Braves should have won.

+1. I will never forget the 96 series. Up 2-0 in the 8th inning and Leyritz took Wohlers deep to tie the game at 6....the Braves lost it in the 10th and the rest is history.
 

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