Frye returned to Pride in February 2002, facing long-time rival Ken Shamrock at "Pride 19" in a fight he had been trying to trash-talk himself into ever since Shamrock had defeated Dan Severn at "UFC 6". Frye got the edge on a series of clinch battles, while Shamrock dropped down for an ankle lock and transitioned into both a kneebar and a toehold, wrenching Frye's leg badly; however, despite the damage, Frye refused to tap out and managed to knock Shamrock down in a subsequent punching exchange. The bout moved to the mat, where Shamrock attempted another ankle lock, only for Frye to try to counter with one of his own and finally refusing to tap out until time ran out. After an exciting and hard fought battle, Frye pulled out a split decision victory. Even though Shamrock had injured Frye's ankles, later leading to dependency on painkillers, the two hugged after the fight ended, putting an end to their rivalry. Many MMA fans agree that both fighters were never the same again, as both their careers began a steady downturn after the fight.