When has a musical with a forgettable and weak score won Best Musical?"
Many. We can start with Kinky Boots.
That was my first thought as well. Not to mention that a "weak score" is purely subjective, so personally, I'd add Memphis, The Producers, Raisin, Applause, Hallelujah Baby, and Redhead to the list. And perhaps a few others, depending on the criteria. Based on how much of the score is committed to memory upon leaving the theatre and/or hearing it for the very first time, I'd also add others like Hamilton, Dear Evan Hansen, Fun Home, Gentleman's Guide, Billy Elliot, In the Heights, Spring Awakening, Passion, Mystery of Edwin Drood, Nine, Two Gentlemen of Verona, Fiorello and Wonderful Town where I couldn't pluck a tune out of thin air after the first time I ever heard the scores.
And you think Kinky Boots has a forgettable and weak score? Apples and oranges, my friend.
"Apples and oranges"? That doesn't make sense in this context.
"What can you expect from a bunch of seitan worshippers?" - Reginald Tresilian