Hmmm... I don't think Madara should be on this list, his timeline's messed up. He was resurrected in his prime but he already had the Rinnegan, even though he got those when he died. It means Kabuto messed with him and we can't really tell his age.
As for the rest, I think Kakuzu. I'm pretty sure Kakuzu fought Hashi before Madara managed to make a clone of him.