Obi (Snow White) vs Tomoya Okazaki

Tomoya is a good guy who knows how to fight when needed but Obi is a trained professional. He will be able to get the win rather easily with or without a weapon. When you have two characters without any special abilities, the trained fighter will win 9 times out of 10. There just isn’t anything Tomoya can do to try and turn the tides of battle. Obi (Snow White) wins.

Tomoya Okazaki vs Caillou

Tomoya Okazaki isn’t the most athletic character anymore because of the injury to his arm but he would still be able to take Caillou down rather quickly. Tomoya has the age advantage and he seems like the kind of guy who wouldn’t mind getting into a bit of a fight. Caillou doesn’t have that same mindset and would end up just being overshadowed here. The fight won’t last long. Tomoya Okazaki wins.