It does matter. A person with skill has a higher probability of winning than someone without skill. There are two sequential checks... first, the check that the user is not in control of, the "will the game let you win" check, then the "did the player use enough skill to win?" check.

Let's say the game only allows 1/100 tries to have the chance to win. Player A has the skill to win 50% of the time, player B 25%.

Player A will end up winning 1/200 times, while player B will win 1/400.

Skill matters.