In terms of actual assault or rape, it just might. The potential confusion as he approaches can lead to a costly moment of indecision in which he'd have time to silence her.
But rape isn't the only problem, there are other crimes that can be committed, such as sexual harassment and indecent exposure. Sexual assault can even occur and the woman might be afraid to say something because it's her word against his, remembering that sexual assault can be something as brief and unprovable as groping a butt or breast.
If she complains about something like that to management or the cops, he can just say she's a transphobe making up stories to get him in trouble.
And with biological women being dehumanized by the trans movement these days, it's not out of the question that the woman could be arrested and charged, especially here in Canada.