I really feel like Nagatoro is going to lose, or rather she has to now that Hachiouji did, which would be a better way to finally bring this never-ending confession arc to a close. If they both lose it shows them both that sometimes effort just isn't enough, there will always be someone better. In recognizing that, it may serve to bring them closer together. Or at the very least, show Hachiouji that even Nagatoro can fail too.
I feel like if she won, it would leave a lot of Orihara's story unresolved and possibly even inflame insecurities in Hachiouji, seeing as she won her battle where he lost his. In spite of what he told her, he may not feel like he's good enough yet and hold out confessing.