With invasions XD. It was painfully hard.
For me it would be Hard Balls from Pursuit Force and Jecht Final Summoning(FFX final boss).Both of them took me weeks to finally find a way to beat them.They were trully wore my mind and body down.
Edit: Oh and Misterious Figure from Kingdom Hearts Birth By Sleep.That guy was freaking OP wioth his 1 hit kill.Again took me weeks to finally beat him, and I only manage to kill him once.
My (locked) thread about how difficulty should be a decision for the developers, not the gamers.
https://gamrconnect.vgchartz.com/thread.php?id=241866&page=1
No Heart - Kingdom Hearts Birth By Sleep. I don't even know how I was able to defeat him.
Also, Li-Grim - Final Fantasy TACTICS Advance. That thing was a bitch.

Souls series are a real challenge, specially watchdog but I could beat them.
I still don't know what was the issue but I couldn't ever kill Uncharted 2 Lazarevic on Crushing. I had to ask my girlfriend to kill him for me, true story.
I don't know probably one of the later bosses in either Zelda 1 or 2, I remember having a lot of trouble with the Thunder Bird in Zelda 2. The d*mn thing is harder than Dark Link (even without cheating)!
I have two :
DS3 Nameless King
Last boss in Eternal Champions. In fact I managed to eventually beat Nameless King but the same cannot be said for Eternal Champions Boss.
The thing about Eternal Champions was, unlike other beat em ups, if you lose a fight, it sends you back to the previous round.
https://youtu.be/vaiXRQPPu2k
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