ニュー・エイジ・アウトローズ
Gunn then began a brief feud with The Rock. At SummerSlam, The Rock defeated Gunn in a Kiss My Ass Match. Following this, Gunn then briefly feuded with Jeff Jarrett for the Intercontinental Title before reuniting with Road Dogg to reform The New Age Outlaws. The Outlaws won their fourth tag team championship by defeating The Rock 'n' Sock Connection in September 1999. The Outlaws later reunited with X-Pac and Triple H to reform D-Generation X. During this time, The Outlaws won their fifth Tag Team Championship after defeating Mankind and Al Snow. At the 2000 Royal Rumble, The New Age Outlaws retained their title against The Acolytes after interference from X-Pac. The Outlaws then had a feud with The Dudley Boyz, who won the Tag Team Championship from The Outlaws at No Way Out. After suffering a torn rotator cuff in the match with The Dudley Boyz, Gunn was kicked out of D-Generation X for "losing his cool" to explain his impending absence to recover from his injury.