Here are some of the most heart-breaking or disgusting losses I've been part of.
Semis 2002, Furious George 17-16. Well, when you turn it over three times in a game, you really don't deserve to win, you know. But this would be the only game on this list that would also qualify for my "top 10 all-time games, win or lose." You hear people say, "It doesn't matter whether we won or lost, I was just happy to be part of this game," but 9 times out of 10, they won. #1 heartbreaker. In a way, it's too bad that this game happened, because now everyone thinks this is closer to the norm instead of a more realistic 15-20 TOs per team.
Semis 1993, NYNY 21-14. We just fell apart after a little brouhaha. We'd been doing pretty well against them that year, losing at Cuervo and Easterns, but winning most of the other games, including two 7-point wins in a row. But we were dicks, they were dicks, and it just didn't work out for us. On the bright side, it led directly to DoG. Perhaps one of these days I'll construct an alternate universe in which we won this game.
Finals 1992, NY 21-13. Up 10-8, down 17-11. We were close to evenly matched that year, I think, unlike the next year, when we would have been the clear favorites.
Summer league finals, 1999, Gretzky 15-14. This is more disappointing than disgusting, although it is that. I'm throwing this in as a favorite to Wicks and the other 12 players on his team that year who also played at Nationals. Congrats, you beat a bunch of old drunks. The disgusting part of this game is that none of us (save the one who made the decision) knew that the game was capped at 15 until we were about to pull at 14-14. I will also point out that Nathan made the best play of his career in this game. Briefly, he heard me call for the give and go and left his guy standing in the middle of the endzone to run 30 yards to make a block, while the rest of my team was watching him saying, "What is that guy doing?" But for a "man on" call, this game would have made it to last week's "Best meaningless victories" list.
Game to go, 1986 Mid-Atlantic Regionals, R&B 19-15. I was attending college in Cleveland but skipped out on them to play with my hometown Pittsburghers, as I thought this might be my best and last chance to make it to Nationals before I retired or got old. We were up by 3 at half, I think, before being overcome. I was the deep in the 1-3-2-1 zone. Ironman launched some bottle rockets over our heads that tournament.
Cuervo 1992 finals, NY 15-14. You would think that a 14-9 lead with 6 minutes left before a semi-hard cap (finish the point, if one team is up by 2 or more, game over) would be safe, but you'd be wrong. Everyone remembers Alex's "$2000 turnover", but there was also Griff's throw out the back, Joey's failed toe drag (he should have done the scissor-kick!), and us getting beat on some 2-pointers. A chickenshit timeout call would have won the game, as would have a zone defense, or a goal. But again, history would be different, blah blah blah.
Fools 2002 semis, WesWill by a few. Up by 4 or 6, and the Short Fat Guys fell apart. More disgusting than heart-breaking.
Goaltimate II, 21st Century DoG over Wellesley Founders, 3-0. 3 games to five over in 28 minutes, allowing only one goal. In a horrible conflict of interest, they had Steve Mooney officiate the game, and six of their team were current teammates with Steve. Mooney made an early "illegal zone" call against us, dooming our innovative defensive structure which had propelled us the previous year to one of the richest cash prizes in frisbee history. Another factor against us was that we were older and it was our fourth round of the day, with one of the earlier rounds going well past the cap. I had started cramping in that round, too, not a good sign if the guy who did most of the clearing was cramping in the second round. This probably was the most disgusting, self-loathing game I've been in. Embarrassment to this day.
Worlds 2002 finals, Condors 14-12. Up 8-4. I was having a great game up until committing our final two turnovers. The staff also screwed up the time cap, but that didn't affect the game, just added to the bitterness.
GOAT Tuneup 2003. Lost to 9 guys in the heat, forcing maybe 2 turnovers the whole game.