I came up with a scenario to put Punisher into a real challenge.

Spiderman is looking at the news to see a vigilante named punisher is wreaking havoc. He thinks he's a bad guy and decides to take him down. He has very low expectations about punisher and thinks it will be fairly easy. Punisher somehow finds out about this and decides to prep up for the encounter.

To give frank an advantage. This takes places in the hideout back in season 1 of punisher. He gets a week of preparation. Frank sets traps and everything with loads of guns. He is not looking to kill spiderman perhaps just knock him out or severely injure him so he can get away. So he suits up. If Punisher needs it then he obtains "Judas Bullets" for an advantage. Peter is confident about taking him down.

@achievedhero: is this a battle or...?

Peter is still rather inexperienced and not ready for a scenario like this. He hasn't received Avengers training like the rest of the modern recruits.

If his Spider-Sense works, I'm betting on him, otherwise he gets a bullet in the head.

@anthp2000: Agree 110 percent He can outsmart beat at his game with knowledge on Pete and what he can do frank will come up with something to stop him dead in his tracks

Punisher should logically be able to pull it off with prep.

Punisher.

Spiderboy is squashed

The Punisher wins.

@rebake: Sort of but it's a discussion deciding if spider man can take on a prepped punisher.

I'm siding with spider-man. No way is Frank going to want to harm a kid and with Peters durability and strength it would be really hard to incapacitate Peter without harming with the weapons and tactics we've seen from punisher. If Frank was willing to kill I can see this differently due to Peter's inexperience and Franks prep and Peter going in all cocky. But I don't know what Frank can do to stop him that wouldn't do severe damage to spider-man.