This is the size we're talking about here:
A the squids preferred depth, the squid. On land or in shallow water the size would be a detriment, and the hippo would KO Squidward's chonky cousin with ease.
He probably ment shallow waters for hippo to stand any chance
Then hippo by default 100%. The giant squid evolved under the immense pressures of the deep, it would die immediately if brought near the surface. Even if it didn't, it's relatively slow moving as far as animals go, again, evolved for the dark, cold deep where conserving nutrients is paramount to all else.
What if the hippo was funded 80 billions dollars from the us military and was given himars
Mythbusters once did an episode and determined that at deep ocean pressures, a human scuba diver without active air pressure from topside can be squeezed entirely into their helmet.