head to head
Neither is harder. They score identically on all four axes, so the difference between them is in kind, not degree.

Execution · Pure Mechanics
A run-and-gun boss rush about dodging scripted patterns with tight inputs.

Execution · Pure Mechanics
Co-op bullet-hell shooter set in a 17th-century British colonial Mars.
Cuphead leans Execution (Pure Mechanics); Jamestown: Legend of the Lost Colony leans Execution (Pure Mechanics).
Same score on execution - which means the number cannot separate them. The difference is in what each one asks of you.
Cuphead
Tight dodging and parry timing decide every boss.
Jamestown: Legend of the Lost Colony
Bullet-dodging precision at high difficulty
Same score on reads - which means the number cannot separate them. The difference is in what each one asks of you.
Cuphead
Bosses cycle scripted phases; no adaptation to player.
Jamestown: Legend of the Lost Colony
Bullet patterns are fully scripted
Same score on variance - which means the number cannot separate them. The difference is in what each one asks of you.
Cuphead
Minor attack-order shuffling between phases.
Jamestown: Legend of the Lost Colony
Deterministic waves every run
Same score on optimization - which means the number cannot separate them. The difference is in what each one asks of you.
Cuphead
Loadouts and boss phase order are fully learnable.
Jamestown: Legend of the Lost Colony
Vaunt-chaining score systems and route memorization
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.