Shortly after his feud with André had ended, Roberts entered into a feud with Ted DiBiase. Instead of fighting for the Intercontinental Championship, the prize of the feud was DiBiase's own Million Dollar Belt. It was at this time that Roberts' problems with the discs in his back were publicly acknowledged, as DiBiase attacked Roberts after a victory over his bodyguard Virgil on "WWF Superstars of Wrestling". In the attack, Roberts was (storyline) injured by DiBiase and needed time off to have surgery to repair the damage. Roberts returned and feuded with DiBiase throughout the end of 1989 into 1990, including a point where Roberts stole DiBiase's Million Dollar Belt, daring him or Virgil to reach into the canvas sack where Damien was to retrieve it. The culmination of their feud took place at WrestleMania VI at the Skydome in Toronto, where in a match where the Million Dollar Belt was on the line, DiBiase gained a count-out victory over Roberts, thus regaining his non-sanctioned title. After the match, Roberts mounted an offensive against DiBiase and Virgil and then began giving away DiBiase's "money" including giving some money to actress Mary Tyler Moore who was seated at ringside.