User blog comment:Crimson and Darkness/Volume 25 discussion blog/@comment-32252462-20180321143728/@comment-24595619-20180321211442

Cao Cao underestimated Issei numerous times, which is what led to him being defeated both times. And using his True Longinus he stopped Apophis, Armies of Mass-Produced Evil Dragons and Fake Scale Mails all at the same time.

Apophis died because he stood still and attempted to take on both Infinity Blaster and Longinus Smasher. Just because Issei is powerful doesn't mean that he can match people in terms of pure technique types.