Bates later lost to Sedreck Fields, Kirk Johnson, Leo Nolan, Brian Minto, and Ray Austin before his first retirement.
[citation needed] Bates was persuaded to postpone his retirement when he was given an opportunity to fight four-time heavyweight champion Evander Holyfield.
On August 18, 2006, in a 10-round bout at the American Airlines Center in Dallas, Texas, 44-year-old Holyfield dominated the fight which was stopped in the second round after he landed around 20 consecutive punches on Bates.
Bates would come out of retirement to face Guillermo Jones, Andrew Golota, Odlanier Solis, Kevin Rainey, and most recently Kali Meehan.
Bates got his third victory at OCW on January 10, 2009, at the New Year's Bash by defeating NWA All-Star Wrestling Heavyweight Champion "Pretty Boy" Stan Lee.