Most depressing or crushing loss in a sport you don't usually care about?
2005 NBA Finals. I don't normally watch basketball, but the Pistons were defending champs and played a defensive game which made things a bit more interesting for me to watch. One of the games, Robert Horry hit a last second shot to win and that specific loss was the worst one.
Worst loss in a game or series you were 100% sure you were going to win?
The 2009 Stanley Cup finals come to mind when the Red Wings were up 3-2 but then lost the next two games, both by just a goal. They had beat the Penguins the previous year and seemed set to do it again coming in.
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ONLY FIVE CAN LADDER.
Sushi, kamikaze, fujiyama, nippon-ichi...