Challenging Players

A lot of the time when I challenge a player, I beat their time MULTIPLE times, and when I’m lucky, it’ll let me win when I beat their time. Can someone please explain why I get a faster lap but still get 2nd.

Are your lap times invalidated? That is, do they have a triangle with an exclamation mark beside them? If so, their lap it likely clean and yours is not; therefore, you did not beat their leaderboard time.