head to head
Neither is simply harder - they are hard in different places. Pokémon Diamond Version demands more variance; Portal 2 demands more execution.

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

Optimization · Pure Optimization
A first-person puzzle game where seeing the solution is the whole skill.
Pokémon Diamond Version leans Optimization (Pure Optimization); Portal 2 leans Optimization (Pure Optimization).
Portal 2 leans clearly harder on execution.
Pokémon Diamond Version
Menu battles need no dexterity
Portal 2
Portal placement requires some precision but timing is lenient.
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 2
No opponent; puzzles are static.
Pokémon Diamond Version leans clearly harder on variance.
Pokémon Diamond Version
Encounter and crit rolls are bounded, mappable randomness
Portal 2
Puzzles are deterministic with no randomness.
Portal 2 leans a little harder on optimization, though the gap is small.
Pokémon Diamond Version
Physical-special split deepens solvable team building
Portal 2
Solving the puzzle's logic IS the entire game.
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.