Kaguya Shinomiya is rich, smart, and very quick to react to each and every situation. It’s fair to say that Rosie would not be able to compete with her here. The age difference is already pretty massive but beyond that Kaguya is just very skilled at a variety of fields including archery. She should be able to win this match within mere moments and then move on to the next challenge. Kaguya Shinomiya wins.
Kaguya Shinomiya vs Rosie (Caillou)