Taking a young Triple H under his wing may have had more to do with Regal's backstage process than anything else, but their relationship still managed to take on a life of its own. When Triple H got an opportunity to sign with WWF, Regal encouraged him to do so as he thought the work would help Triple H improve.

Regal returned to WWF in 2000, but he didn't get much screentime with Triple H until feuding with Evolution, a heel faction headed by Triple H. The former partners had their first singles match against each other in 2004, but their first mini-feud is best known for Triple H's brutal attack on Regal backstage.

In 2008, Regal inserted himself into the King of the Ring tournament, despite being the show's general manager, and ended up winning the event. He was set up as the heel focal point of "Raw" with another feud with Triple H, but Regal was suspended for 60 days due to a wellness violation that he still doesn't understand.