This reminds me a bit about the competitive atmosphere in Kaguya-sama with declarations of who won or lost at the end of the chapter, except the "competition" here is only one-sided and protagonists are both dorky idiots.
Rintarou's a meathead for sure, but fashion sense aside, given he's got enough rizz that girls are confessing to him, that makes him a certified himbo.
Giving Ino a win here probably helps salve her injured pride about the whole losing to his confession thing, so the more "W"s she gets the sooner they might start dating for real.