Been spending most of my time on the women's board lately, but I've been a fan of the men for longer, so reading this thread all the way through was like reopening a bunch of old wounds and pouring in salt. For me, the bad NCAA Tournament losses are always worse than any others. The 6OT debacle annoyed me to no end, but at least there was a chance to regroup after that, and eventually reach the Final Four. Watching an entire season come crashing down and die right before your eyes is another beast entirely. And most of those pre-1999 losses, from back when we had the most tournament wins of any program never to reach the Final Four (and every successive loss made it feel more and more like we were snakebitten and might never get over that hump), are still more painful for me to think about than almost anything that's happened since 1999. Here's what sticks out in my memory:
1990 - This was the absolute worst, and not just because I was in 5th grade and it was the season when I first became a UConn fan. Such an unbelievable run by our Dream Team, and Tate's miracle shot against Clemson, the whole deal, and then to watch all the magic and euphoria of that whole season suddenly guillotined by that Duke dou¢hebag with the stupid hair. That game broke my heart in a way that none of these other games could. I swear that the loudest chorus of boos I've ever heard in Gampel Pavilion was on 3/29/99 when CBS cut to that Duke guy's face in the crowd at Tropicana Field. We never did manage to pay him back, but we finally exacted some sweet revenge on his school on that night.
1994 - Gut-wrenching, and such a missed opportunity because UNC's upset loss had blown our path to the Final Four wide open. I remember futilely saying a prayer to help Donyell hit one of those free throws. Didn't work. Just a devastating loss against a team we should have beaten. This game was still on my mind when Shabazz and co. stormed back to wreck Florida's season in the Final Four 20 years later.
1995 - I think I've actually suppressed any specific memories I had of this game. I can understand why folks are saying it was a great game and we just got beat by a better team. But this was probably my favorite of the mid-90s UConn teams, and I despised Harrick and that UCLA team, so this one really cut a deep scar. Of all these losses, this is the one that makes me wonder what might have been, because our guys were playing at such a high level when they got knocked out. I still want to throw a grenade at my TV every time I see the final play from that bleeping UCLA-Missouri game, because I think that cost us a legitimate shot at a title.
1996 - This was such an uninspired, lackluster, discouraging loss against such an inferior team that I couldn't bear to watch the rest of that year's tournament. And it was just a sad way for Ray's college career to end. There are only two things that make this game a little easier to take, in hindsight. One, as someone said above, we'd have been forced to vacate any additional wins in any event. And two, this was simply not the same team after Ricky went down—recall that we struggled for long stretches against Eastern Michigan in the second round as well—so I don't think we would've gone much further anyway, as poorly as we were playing.
1998 - We were a young team on the rise and not as good as UNC, so it was hardly surprising that we lost. Mostly I remember being pissed at the committee for putting us in their region because I thought we deserved better, and I still think we might've cracked the Final Four that year if we'd been given a fairer draw.
1999 - Everything changes, obviously.
2002 - I don't remember this one hurting all that much; it felt kind of like 1998 in that we had a good run but just ran into a more talented, experienced team and couldn't quite topple them. I'd probably have felt worse about it if I'd known Caron wasn't coming back.
2005 - Worth a mention only because this team had a lot of talent, and a second-round loss to a #10 seed isn't a great way to go out, but I think the fact that we'd just won the previous year helped take the sting out of this one.
2006 - I'm going to be in a tiny minority here, but while this game annoyed me quite a bit, it didn't actually hurt that much. I spent months yelling at my TV, imploring that year's team to show some heart to match its talent. Finally, as we were in the process of blowing a huge lead against Notre Dame in February (even though Williams saved us with a triple-double and we eventually won in OT), I consciously reached the sad conclusion that we absolutely did not mentally have what it took to win a championship. I made my peace with that fact and spent the rest of that season quietly watching the rest of the games, with no doubt in my mind that we'd fall short in the end. When it finally came to pass against George Mason, I simply shook my head and thought, "well, at least it wasn't against Albany."
2008 - This pissed me off mostly because Calhoun had never lost a first-round game as our coach before, and I'd always loved that fact. A.J.'s injury just threw a monkey wrench into that game, and even though we still had a chance, too many things just didn't go right in the end. Frustrating.
2009 - I felt we were legitimately outplayed here, but it was annoying primarily because I resented our having to play a de facto road game in the Final Four against a lower-seeded opponent. (So, did I feel bad five years later when MSU had to deal with us at MSG? Nope.) I think this team, if healthy, would've had a fighting chance against UNC or anyone else that year, but our defense was never quite right again after we lost Dyson. The MSU loss hurt a little less because I was so proud of our guys for shaking off the 6OT fiasco and fighting their way to the Final Four at less than full strength.
2012 - Tough to get too upset or feel too awful when the team puts forth that pitiful an effort, especially in a theoretically even 8/9 matchup. It just sucked that this turned out to be Calhoun's last game, because he deserved better than that. Still happy that we could pay ISU back two years later.
Sorry for the excessive length, but I found this strangely cathartic and got a little carried away.