head to head
Neither is simply harder - they are hard in different places. NFL Head Coach 09 demands more reads; The Elder Scrolls V: Skyrim demands more execution.

Optimization · Pure Optimization
An NFL management sim about roster building, scouting and game planning.

Optimization · Pure Optimization
An open-world RPG mostly about discovering and stacking exploitable progression systems.
NFL Head Coach 09 leans Optimization (Pure Optimization); The Elder Scrolls V: Skyrim leans Optimization (Pure Optimization).
The Elder Scrolls V: Skyrim leans clearly harder on execution.
NFL Head Coach 09
No on-field input; pure management interface
The Elder Scrolls V: Skyrim
Combat is forgiving; aim and timing rarely punish you.
NFL Head Coach 09 leans clearly harder on reads.
NFL Head Coach 09
AI opponents scripted; light playcall prediction
The Elder Scrolls V: Skyrim
Enemy AI is scripted and exploitable; not adaptive.
NFL Head Coach 09 leans clearly harder on variance.
NFL Head Coach 09
Draft prospects, injuries and game sims carry hidden uncertainty
The Elder Scrolls V: Skyrim
Loot tables and leveled lists inject mild randomness.
NFL Head Coach 09 leans clearly harder on optimization.
NFL Head Coach 09
Roster building, scouting and game planning are the whole game
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.