His first major rivalry in the cruiserweight division came against Yoshihiro Tajiri as the duo competed against each other in a series of matches in the first half of 1999, where the duo exchanged wins on "Hardcore TV", supercards and the Guilty as Charged and the Living Dangerously pay-per-view events. Crazy followed with participation in a series of matches with international cruiserweights as he racked up wins against fellow luchador Mosco de la Merced at CyberSlam, Japanese wrestler Taka Michinoku at Hardcore Heaven while losing to Italian Little Guido at Hostile City Showdown and defeating him at July's Heat Wave pay-per-view.