ROUND ONE: Kirby & Eren Jeager vs. Harry Potter & King Dedede
Dedede is the weak link in this match. Tough? Yes. Strong? You betcha. A talented fighter? Absolutely not. Dedede's moves are deadly, but hopelessly predictable. He often has to ready himself or charge himself before delivering an attack, effectively telegraphing his moves to his opponents. That said, Dedede could take the physical damage while Harry Potter stands in the back and casts spells.
As KB mentioned, Kirby is extremely susceptible to damage, and if anything hits him the wrong way, he's going to lose a health bar. However, KB was wrong about how quickly Kirby can learn a new ability. When Kirby swallows an enemy, he's able to use their abilities instantly. What's more, Kirby actually already has experience using magic (http://kirby.wikia.com/wiki/Magic), so if he's able to swallow Harry or one of his spells, Kirby should be able to start launching magical attacks of his own.
Right now I'm leaning towards Kirby and Jeager since Kirby is probably more experienced fighting magic users than Harry is at fighting power-copying pink puffs, but I could certainly be swayed to vote for HP and Dedede.
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