Any time you know the rules and can achieve a checkmate, given the opportunity.
When I, as an adult, began studying piano I was awful in my first recital. My teacher said, "Don't apologize: there is no such thing as bad music."
Some years later in the adult program, I passed the audition to play Schumann's First Sorrow at the ACE Recital of the world-class Peabody Institute of Johns Hopkins University. Opera Grand Diva Hyunnah Yu approached me after the recital and said she was moved by my playing.
That pleased me, because I knew I made mistakes playing it in terms "rubato" -borrowed time: I should have stretched the duration of certain notes, stealing the time from neighboring notes, to make the piece feel more natural and emotional.
Likewise in chess, it's just as likely you will mistakes playing a chess game with a rating of 2000 or a rating of 500. The complexity of the mistake is the only difference.
It's a great question... I guess my answer has to be yes ... Just not very well.