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If Taskmaster scales to Captain America then Luffy is stronger. He no-sells attacks stronger than 400 Tons and can generate 650 Tons with attacks like Gomu Gomu no Storm.

Taskmaster is able to mimic and predict Luffy's movements and he could beat him if he uses his sword. But Luffy is prone to disarm his opponents and even break their weapons so Luffy would grab his sword and his shield and will break them.

Luffy is not as skilled as he is later in the series so that's a good advantage.

In a battle of stamina Luffy is the clear winner.

This is pretty close, but Luffy is stronger by a good margin, has more range, stamina and Lifting Strength to take Tony's weaponry to break them. Once it comes down to that, no martial art will help him to bypass Luffy's resistance to Blunt Force.
 
I think he should. The pressure points should bounce back the strike. Since all of his body is rubber his nervous system and stuff is made of rubber as well.

This is confirmed since the usage of the Gears are only possible if the insides of his body were made of rubber as well. I also don't see Pressure Points in Tony's profile but one of his weaknessess is that he loses previous memories when learning something new so I don't think that's a reliable winning condition.
 
Luffy FRA, the sword is a problem, but since it is IC to Luffy disarms or break their weapons, i think he will get the win, even when he can't match Taskmaster's skill
 
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