Kaguya is a very capable strategist but she’s not going to be able to take down Oz. Oz is trained with the sword to an extent and has his contract with the B Rabbit. Kaguya’s archery can be a really good long range option to be sure but it’s not quite as good as the sword. Granted, in cases where you are really expert with the bow you can pull off the win but ultimately this isn’t that matchup. Oz Vessalius wins.
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.