head to head
Neither is simply harder - they are hard in different places. Gloomhaven demands more variance; Portal demands more execution.

Optimization · Pure Optimization
Sprawling tactical dungeon crawler where managing a dwindling hand of cards decides everything.

Optimization · Pure Optimization
The portal-gun puzzle game whose solutions are everything.
Gloomhaven leans Optimization (Pure Optimization); Portal leans Optimization (Pure Optimization).
Portal leans clearly harder on execution.
Gloomhaven
Turn-based; zero dexterity demand
Portal
Portal placement timing modest.
Gloomhaven leans a little harder on reads, though the gap is small.
Gloomhaven
Monster AI follows printed, mappable rules
Portal
No adversary modeling player.
Gloomhaven leans clearly harder on variance.
Gloomhaven
Modifier deck and monster ability draws
Portal
Deterministic chambers; no randomness.
Gloomhaven leans a little harder on optimization, though the gap is small.
Gloomhaven
Card economy and scenario routing are the game
Portal
Pure puzzle-solving optimization.
A matching score does not mean a matching test. Two games can both sit at 10 on execution and demand completely different things of you - which is why the reasoning above matters more than the number beside it.