This is my list too, but I’d also throw Forty-one-Donut onto the pile.
Yup, you said it all. 2003 was awful, but winning it all in 2004 and 2007 made it all OK.
I still say there was holding on the Helmet Catch play.
Knicks fan. 1993, theCharles Smith game
Christian fucking Laettner.
As a Cubs fan, I have plenty to choose from. There’s the infamous “Bartman game” from 2003, the collapse against the Padres in 1984, the last month of 1969…
But I’m going with Wednesday, September 23, 1998.
The Astros had run away with the NL Central, but the Cubs were locked in a fierce 3-way battle for the wild-card spot with the Giants and Mets. With 4 games left in the season, my friend and I took the day off and drove up to Milwaukee to cheer on our Cubs against the Brewers.
We watched the Cubs take a 7-5 lead into the bottom of the ninth, but the Brewers managed to load the bases with one out. A pop foul provided the second out. Then, Geoff Jenkins stepped to the plate and lifted a high, lazy fly ball to left. A routine catch would win the game. Brant Brown camped under it and – dropped the ball. All three runners scored, and just like that, a victory had turned into an 8-7 loss, as the Cub fans in attendance stared in disbelief.
The Cubs did end up winning the wild-card, but it took a one-game playoff against the Giants to get it done. They then got swept by the Braves in the first round of the playoffs. We’ll never know, but that series may well have gone differently if they didn’t have to play that 163rd game – they lost a day of rest, used their ace pitcher, and arguably used up all the fight they had in them before they even got to Atlanta. Who knows what may have happened if Brown had just held on to that damn ball…
Last game of the regular season, 1987: Tigers 1, Blue Jays 0.
The 1992 NLCS. Game 7: The Pirates took a 2-0 lead into the 9th, and after giving up 1 had the Braves down to their final out. Ultimately, Sid Bream, one of my favorite Pirates ever, but playing at that point for the Braves, gimped around from 2nd to just barely beat the tag for a 3-2 win.
The Pirates have not had a winning season since then, setting a record for all of professional sports that they added to this year.
1993 NCAA Basketball Final.
North Carolina beats Michigan with Webber’s famous time-out.
Nearly killed me.
Super Bowl V. Baltimore vs. Dallas. Ripped out my 15 year old heart when O’Brien made the field goal. Later I would number my race cars #74 after Bob Lilly. Can’t stand the the Cowboys today.
PS. Yes, my userid is racer72. I was a huge fan of Benny Parsons too. I used this number when I raced online.
1999 World Cup Final, Pakistan v Australia. Will never live it down, abject surrender.
Watching the Celtics choke in Game 7 of the Finals last year was brutal. They were the storybook team, the aging team that nobody thought would even make it to the playoffs, the guys who just inched in by the skin of their teeth and then DOMINATED through grit and teamwork. They needed to win only one of the last two games to be crowned champions. And then they were destroyed in Game 6… but that was OK because there was still Game 7. And then they led for most of Game 7, and victory seemed within reach, but the Celtics kept giving the Lakers chance after chance after chance until finally their complete ineptitude at getting rebounds caught up with them and they sank into oblivion with just minutes to go.
Argh. That fucking sucked.
Argh… Mark Wohlers and Jim Leyrtiz…
My Braves misery goes back to game 7 of the 91 World Series. Freaking Lonnie Smith falling for a decoy play at second when he should have scored easily from first on a double. Braves loaded the bases with no outs, and couldn’t score.
Game 6, 1994 Eastern Conference Finals between the Rangers and Devils.
Devils lead the best of seven series 3 games to 2, and have a chance to clinch a Stanley Cup Finals berth for the first time in team history, finally shaking off the the label of “a Mickey Mouse organization” given to them by Wayne Gretzky after his Oilers thoroughly demolished them some years before.
Before the game, Mark Messier, the Rangers Captain, guarantees a victory.
With the Devils leading 2-1 after two periods, the jerk goes and nets a hat trick in the third period and makes good on his word, leading the Rangers to a 4-3 victory and tying up the series at 3 games apiece.
This is followed very closely by Game 7 of the same series, in which Stephane Matteau scores on a wrap-around early in double-OT to end the series and send the Devils home. Howie Rose’s “Matteau! Matteau! Matteau!” still hurts to hear, even these 16 years later.
Fortunately, the Devils went on to win the Cup the following year, and a couple more times after that–and the Rangers haven’t so much as sniffed a Finals appearance since 1994–so it doesn’t sting quite as bad as it did, but man did that one hurt.
http://www.youtube.com/watch?v=GxmaDwKtHyw 1987 Pistons whipped the Celts until Isiiah did the dumbest thing possible. I was shocked. Any other thing he did would have been better.
The video was a bit fuzzy - what did he do, give the inbound pass to Larry Bird?
I will say that the '96 World Series loss was probably my fault, for being the biggest douche in my life after the Braves won the NLCS after being down 3-1 to the St. Louis Cardinals.
What did I do? I called random numbers in the St. Louis area code and, in the rythm of the “Tomahawk Chop”, went “Haaaaw-haw-haw. Haaaaaw-haw-haw” to whomever answered.
Haaaaaw-haw-haw, indeed. 
1993 Notre Dame v. Boston College: Just an unbelievably heart-wrenching loss that cost them (unfairly*) the National Championship.
2010 Butler v. Duke: I’m not a huge Butler fan, but I live in Indianapolis, and it’s really really hard to not root for a team like the Bulldogs. I thought they were a legit Final Four team going in, and when they made the National Championship game, I had to get tickets (when there are 70,000+ tickets to go around, it’s not all that hard). It was a great game, it cemented my dislike for Duke, and the Bulldogs had not one, but TWO chances to win it at the end. Regardless, it was still a tough “what coulda been” kind of loss. I also think it was easily the largest crowd to ever root for one basketball team in the history of the game. All other big-arena games (like in the NCAA Tourney) are split between teams - but this was Butler’s hometown and they were the huge underdogs.
*You can argue that ND didn’t deserve the championship in 1993 after beating #1 FSU in the regular season, but you can’t then argue that ND didn’t deserve the championship in 1989 (when they lost to Miami, who then lost to FSU).
This. And it’s so pleasant to have CBS dredge it up every single March.
The 1984 Orange Bowl. And thus began a tradition of having solid regular seasons and having to cap it off every year (it seemed) by playing a Florida team in Miami.