head to head
Neither is meaningfully harder - they pose close to the same test. The widest gap is execution, and it is a single point.

Optimization · Pure Optimization
The 2002 Total War pairing turn-based medieval empire management with massive real-time battles.

Optimization · Pure Optimization
Optimising road networks and production chains at a settler's pace.
Medieval: Total War leans Optimization (Pure Optimization); The Settlers II: 10th Anniversary leans Optimization (Pure Optimization).
Medieval: Total War leans a little harder on execution, though the gap is small.
Medieval: Total War
Real-time battle control rewards quick unit handling
The Settlers II: 10th Anniversary
Slow road-laying needs no dexterity at all
Same score on reads - which means the number cannot separate them. The difference is in what each one asks of you.
Medieval: Total War
Multiplayer battles add human feints; campaign AI is scripted
The Settlers II: 10th Anniversary
AI opponents expand on predictable scripts
Medieval: Total War leans a little harder on variance, though the gap is small.
Medieval: Total War
Battle dice, loyalty and event cards add noise
The Settlers II: 10th Anniversary
Map resources are scripted-but-unknown until explored
Same score on optimization - which means the number cannot separate them. The difference is in what each one asks of you.
Medieval: Total War
Campaign economy and battlefield doctrine are deeply learnable
The Settlers II: 10th Anniversary
Road networks and production chains are 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.