head to head
Neither is simply harder - they are hard in different places. Heroes of Might and Magic II demands more reads; The Elder Scrolls V: Skyrim demands more execution.

Optimization · Pure Optimization
Beloved fantasy turn-based strategy of heroes, castles, and stacked creature armies racing for map control.

Optimization · Pure Optimization
An open-world RPG mostly about discovering and stacking exploitable progression systems.
Heroes of Might and Magic II leans Optimization (Pure Optimization); The Elder Scrolls V: Skyrim leans Optimization (Pure Optimization).
The Elder Scrolls V: Skyrim leans clearly harder on execution.
Heroes of Might and Magic II
Turn-based clicking only
The Elder Scrolls V: Skyrim
Combat is forgiving; aim and timing rarely punish you.
Heroes of Might and Magic II leans clearly harder on reads.
Heroes of Might and Magic II
Hotseat duels reward mind games; AI is mappable
The Elder Scrolls V: Skyrim
Enemy AI is scripted and exploitable; not adaptive.
Heroes of Might and Magic II leans clearly harder on variance.
Heroes of Might and Magic II
Map exploration, morale, luck, and combat rolls
The Elder Scrolls V: Skyrim
Loot tables and leveled lists inject mild randomness.
Heroes of Might and Magic II leans clearly harder on optimization.
Heroes of Might and Magic II
Build orders, hero chaining, and creature math are deeply solvable
The Elder Scrolls V: Skyrim
Skill stacking, enchant loops, and exploits are deeply solvable.
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.