After a win, Medina tried to become a three time world featherweight champion by challenging Naseem Hamed for Hamed's WBO title, but he was defeated by Hamed with an eleventh-round knockout on August 31, 1996 in Dublin, Ireland. He followed that loss with a win, and another attempt at winning a world featherweight championship for a third time, this time around in a rematch with Espinosa. held on May 17, 1997. He lost to the Asian champion, this time by an eight rounds technical decision at Intramuros, Philippines. Medina then lost his next fight, by a ninth-round knockout on August 7, to future world champion Derrick Gainer.