head to head
Neither is simply harder - they are hard in different places. Portal demands more optimization; Silent Hill 2 (2001) demands more variance.

Optimization · Pure Optimization
The portal-gun puzzle game whose solutions are everything.

Optimization · Pure Optimization
A psychological horror experience where puzzle knowledge and avoidance routing matter more than combat skill.
Portal leans Optimization (Pure Optimization); Silent Hill 2 (2001) leans Optimization (Pure Optimization).
Portal leans a little harder on execution, though the gap is small.
Portal
Portal placement timing modest.
Silent Hill 2 (2001)
Clunky combat is intentional; survival over precision
Silent Hill 2 (2001) leans a little harder on reads, though the gap is small.
Portal
No adversary modeling player.
Silent Hill 2 (2001)
Monsters follow simple fixed behaviours, never model the player
Silent Hill 2 (2001) leans clearly harder on variance.
Portal
Deterministic chambers; no randomness.
Silent Hill 2 (2001)
Some item placements are unknown first time; fixed thereafter
Portal leans clearly harder on optimization.
Portal
Pure puzzle-solving optimization.
Silent Hill 2 (2001)
Puzzle solutions, route knowledge and weapon use are fully learnable
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.