Who would win?

[hoplite14gr]

The only real isssue is the pilum.
It is concidered more effective than a javelin. But is it?
I doubt that its effectve range is more than 50 meters (OK roman renactors can correct me on the details.)
The legion must be slightlty more open order than the phalanx to cast pila.
Would they all find their targets? would they all penetrate?
Linothorax was quite resistant and a hoplite shield with a pilum on it can still do othismos. Plus the "hanging pilum" can still break and stop be the problem on the initial crush.

When the tight formation crushes on the sparse formtation the tighter formation witll gain ground and shove the opposition off the field.

If the pilums were so effective why the romans had problem in Heraklea and why with the exception of the 2nd Battle of Cheronea the wan all their battles vesrus phalanx by turning the flank?

Except in case of Cheronea the only thing that broke the front of the phalanx was another phalanx.
As I said before the only historical case where the legion was pitted against the Italiotic Greek phalanx had the chance to turn the flank.
Kind regards