In June 1999, Bagwell engaged in a rivalry with WCW President Ric Flair and Vice President Roddy Piper after claiming he was being held back. This led to a three-round boxing match with Piper at the Bash at the Beach, which saw Bagwell victorious. In September 1999, he feuded with Berlyn when Berlyn issued a challenge to Bagwell, but at Fall Brawl, Bagwell was late coming to the arena and "Hacksaw" Jim Duggan replaced him. The next night on "Nitro", Bagwell lost to Berlyn after the interference of his bodyguard, The Wall. In November, he defeated veteran Curt Hennig in a retirement match. Bagwell then feuded with Diamond Dallas Page after he made allegations about Page's wife Kimberly. Having spent much of 1999 feuding with older wrestlers, Bagwell was one of the first to join Eric Bischoff's New Blood alliance, forming a tag team with Shane Douglas while both were members. Bagwell and Douglas eventually won the World Tag Team Championship from Ric Flair and Lex Luger, giving Bagwell his fifth World Tag Team Title reign and rekindling his feud with Luger from two years earlier. At Slamboree, Luger defeated Bagwell via submission with the "Torture Rack".