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Who wins

Fight takes place in NYC

Iron Monger wins, with ease.

Iron Monger can win at range if he really unloads with his guns and missiles, but Killian is much faster and a more skilled fighter, plus has the damage output to pick his suit apart. And he's no slouch in the toughness area either. Survived being inside one of Tony's suits after he triggered the self-destruct setting, and could even regenerate entire limbs WAY faster than someone like Fox Deadpool can. And, IIRC, he could even breath fire.

If he gets in close, Killian will win. Mongers' suit can't withstand his offensive output... and it's relatively slow to begin with.

Would back Killian here. Fast enough to dodge projectiles, powerful enoug to chip away at the suit, and can heal the damage. Iron Monger can win, but not for a majority.

Backing Killian as well: Jeff Bridges won't be escaping from a heated limb karate chop-off, meaning his arm or leg goes with the armor piece cut down. Killian's quick enough, has a monster healing factor, etc. He should win.