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

Optimization · Pure Optimization
Solvable team-building progression through Sinnoh's fixed trainers.

Optimization · Pure Optimization
The portal-gun puzzle game whose solutions are everything.
Pokémon Diamond Version leans Optimization (Pure Optimization); Portal leans Optimization (Pure Optimization).
Portal leans clearly harder on execution.
Pokémon Diamond Version
Menu battles need no dexterity
Portal
Portal placement timing modest.
Pokémon Diamond Version leans a little harder on reads, though the gap is small.
Pokémon Diamond Version
Scripted trainers never adapt; online battles are optional
Portal
No adversary modeling player.
Pokémon Diamond Version leans clearly harder on variance.
Pokémon Diamond Version
Encounter and crit rolls are bounded, mappable randomness
Portal
Deterministic chambers; no randomness.
Same score on optimization - which means the number cannot separate them. The difference is in what each one asks of you.
Pokémon Diamond Version
Physical-special split deepens solvable team building
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.