On the November 1, 1999 episode of WCW Monday Nitro, Dean Malenko faced Chris Benoit in a steel cage match as part of the first round of the tournament to crown a new WCW World Heavyweight Champion. The match emphasized their shared reputation as elite technical wrestlers, blending stiff strikes, mat wrestling, and cage-based offense. Malenko used his precision and counters to control stretches of the bout, while Benoit answered with intensity, power moves, and repeated attempts to use the cage as a weapon. Both men traded momentum in a competitive, hard-fought contest highlighted by a dramatic superplex from Malenko and several near falls. Interference attempts from members of The Revolution were teased but ultimately unsuccessful. The match concluded when Benoit climbed to the top of the cage and delivered a decisive diving headbutt, scoring the pinfall victory and advancing in the tournament.
