At Flyweight? I don't know. Calderon was small-ish even for Strawweight standards, at 108 had big problems with Rodel Mayol and Darchinyan was big, heavy handed 112-pounder. He was also just plain better fighter than Segura or Cazares, to me. I think it would quite clearly be step too far for poor Iron Boy. It's unfair to put those two in the ring together.
While I believe Calderon is a better fighter there are weight classes for a reason. Calderon was light hitting and just doesn't have enough weapons to keep the much bigger, much more powerful Raging Bull off of him. Darchinyan by knockout.