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Aizen-san comes to mind, but it's got only 1 heroine anyway

The kuuderes always loose, too.

For kuudere ive seen few

Btw you probably see this one but here you go

@solstice258 that's web comic, doesn't really count

Btw the only instance I see twintail heroine win is "Himegasaki Sakurako is a Hot Mess"