I'm forced to reveal myself as an unfeeling robot, but I cannot remember any loss which made me sad. Every loss made me want to go outside to find someone to punch, but not sad. The closest thing to this was when we were playing MSU in, I believe, 1961. Kuharich was terrible, but our players were so good that we were undefeated anyway. So was MSU and we were rated 1-2 in the country. The game was a bloodbath. Players were being carried off the field on both sides. My "hero" Nick Buoniconti limped off the field at least six times, willed himself back together, and got back in. We lost. I felt sad for Nick--and his superhuman effort. Both teams were so damaged by the game that they won, I believe, a total of ONE game between them afterwards, and finished around .500 for the year. A great unknown player, Tom Hecomovich, our center, never played again. He was having an AA season. Real football...real tragedy...real heroism. This memory probably doesn't count as a heartbreaker of the type that the initial poster wanted, but, who knows what might have happened to both ND and MSU if they had not destroyed each other that day?