On April 24, 1998, Medina joined Carlos De León, Muhammad Ali, Sugar Ray Robinson, Edwin Rosario, Evander Holyfield and a small number of other boxers in the exclusive group of fighters to reign as world champions three or more times in the same division, when he outpointed defending IBF title holder Hector Lizarraga over twelve rounds in San Jose, California. He retained the title on April 16, 1999, in Las Vegas with a nine rounds technical decision over former world super featherweight champion Victor Polo, then proceeded to lose the championship to Paul Ingle.