Which Villain gave The Punisher the toughest fight?

I was curious, which villain do y'all think gave The Punisher the toughest fight and time?

Some immediate examples that come to mind:
- Kingpin beat him when they fought and has been one of The Punisher's longest standing and most hard to kill targets.
- Ares killed Punisher the first time they fought.
- Osborn manipulated and tricked him then years later when he was Secretary of Defense systematically hunted down and killed Punisher (although he had to use a satellite, multiple strike teams, and then send in Daken after Punisher was already fatigued and leg-broken).

- Barracuda and Bullseye both gave him brutal fights that tested his durability and pain tolerance.

- Nicky Cavella made it personal and just really pissed him off.
- Jigsaw and Bushwacker have messed with him a lot but usually doesn't push him to the limits.

- Punisher's fight with The Vulture was pretty gnarly.
- Some of his battles against the Viet Cong in Vietnam left him heavily injured for a time.
- The Hood tormented him by resurrecting versions of his allies like Microchip and dead family through dark magic.

There are plenty I'm missing, but what do you guys think?

I was curious, which villain do y'all think gave The Punisher the toughest fight and time?

Some immediate examples that come to mind:
- Kingpin beat him when they fought and has been one of The Punisher's longest standing and most hard to kill targets.
- Ares killed Punisher the first time they fought.
- Osborn manipulated and tricked him then years later when he was Secretary of Defense systematically hunted down and killed Punisher (although he had to use a satellite, multiple strike teams, and then send in Daken after Punisher was already fatigued and leg-broken).

- Barracuda and Bullseye both gave him brutal fights that tested his durability and pain tolerance.

- Nicky Cavella made it personal and just really pissed him off.
- Jigsaw and Bushwacker have messed with him a lot but usually doesn't push him to the limits.

- Punisher's fight with The Vulture was pretty gnarly.
- Some of his battles against the Viet Cong in Vietnam left him heavily injured for a time.
- The Hood tormented him by resurrecting versions of his allies like Microchip and dead family through dark magic.

There are plenty I'm missing, but what do you guys think?