In Ohio Valley Wrestling (OVW), he formed a successful tag team with Rob Conway, called The Lords of The Ring. The team had a record ten reigns as Southern Tag Team Champions. Dinsmore also held the OVW Heavyweight Championship a record ten times. While still in OVW, Dinsmore also made some appearances as a jobber in the World Wrestling Federation (WWF), first on an episode of Shotgun Saturday Night in 1999. He wrestled in the WWF as Doink the Clown on two later occasions, and as one half of Los Conquistadores (with Rob Conway).