I'm all about the climb and I was too young in the early 80's to appreciate going from not good to great. My first climb, that I truly remember, was the climb back in the 90's. So....
Loss: East Carolina 1999. Coming off a 9 win season the year prior, beating #3 UCLA that year at the end, thinking we were coming back and had turned the corner headed into 1999. We lost to #3 Penn State, the game prior, in devastating fashion but were still ranked inside the top 10 and there was hope. EC game was moved because of Hurricane Floyd. East Carolina came back from being down and stunned Miami. I don't think I ever felt that deflated after a game. There were much worse games but for some reason I never forget how I felt after that game. It wasn't some juggernaut that just outplayed us. It was East Carolina, a game we're not supposed to lose. It felt like the comeback was over and it was never going to happen. Also when the Butch stuff really started to turn bad.
Win: Washington 2001. There has never been a more cathartic experience. After the absolutely deflating 1999 season, the EC game, thinking maybe we have another shot in 2000, and then losing to Washington in the 2nd game. Ugh. Brutal. Especially because the rest of the season was so amazing except for that one blemish. Kept us out the NC game. But then, to take years of frustration out on them in the OB, at night, on national television, in the way we did. My God. It's like 80,000 people in the Orange Bowl, including the players, were going through therapy together. Still the craziest and most blood thirsty I've ever seen the OB.