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Tear Jerker: Digimon Fusion Kai
Matt Ishida's deaths in Season 1. You can shed those manly tears.
"TK… tell… mom and dad… if you see them… that I love them. Tai… please… make sure… Burizalor… pays… for all the Digimon… and the people… he's murdered… he needs to his just desserts… he… must… die by a… Ascendant's hands…"
When the kids return back to the real world at the end of Season 1, their parents happily cried. They have no idea that their kids went into dangerous situations, and some of them (Matt, Sora, and Izzy) were once killed before bought back to life.