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My Opinion: Their both Planet Busters at the same time, due to the fact that Ichigo is hybrid of Shinigami and Quincy, and not forget Hollow too.
While Issei has gotten strong so far in the light novels, their his boosted gear along with the devil reincanation system, and not forget Greats Red Flesh, Diving Copy Gear and Ophis Power. They two can destroy the planet if they wanted too. Uf they went full power it could and endless battle. But i say Ichigo has an advantage since he kill issei with his quincy powers since they creat light simlar to angels, dont forget that is issei is still a reincarnated devil and light is a weakness to devils, lete say Ichigo creates an light weapon and slice Issei, done Isseis a goner the only way that issei csn tank his light weapon is by using his scale mail balance breaker if its strong enough to tank the attack.
