#5 Triple H is undefeated against Billy Gunn (3-0)
Triple H and Billy Gunn have mostly been on the same side during their WWE stints. Triple H took the reigns of DX when Shawn Michaels went on hiatus following WrestleMania 14, and The New Age Outlaws joined the brand new version of the notorious faction. The group wreaked havoc on the WWE roster for years on end, before finally breaking up. Triple H and Gunn did have a bunch of singles matches back in the day.
On April 26, 1999, Triple H and Billy Gunn went at it, with Triple H coming out victorious. A few months later, the two Superstars squared off again on RAW. This time around as well, Triple H defeated Gunn by scoring a pin in the end. Their final encounter would come in early 2001, on RAW. Things remained the same this time around as well, as Triple H pinned Gunn again. Gunn remained a mid-card mainstay on the WWE roster until his exit, while Triple H kept rising up the ranks over the next two decades.