I think it was against Piccolo.
No it was right after goku ate the gomu gomu no mi and became a shinigami
But he got his ass handed to him by Yamcha's bankai and Kamui combo.
Who then died by a saibamen deathnote chidori

Who then died by a saibamen deathnote chidori
What person doesn't know that it was when he faced darth Vader