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Hewdraw is much stronger iirc; he's like 77 Gigatons, while I'm not sure how strong the original Hydra is. Plus Hewdraw can fly and shoot lasers and homing projectiles while the other one can't. Going to say Hewdraw one-shots from a distance.
 
Hydra: 2 (The real cal howard, Iapitus The Impaler)

Hewdraw: 1 (DarkDragonMedeus)

Inconclusive:
 
Yes, but all it takes is for one bite from the Hydra, and the lasers might cut off one of its heads... And anyway, the size of the Hydra is massive, and might be able to reach him before he gets into the air. I'd go with Hydra mid-diff.
 
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