In March 1986, "Fearless", who was (14-13) at the time, took on Roger Mayweather (23-3) at the Sahara Hotel in Las Vegas, Nevada.
Four months later, Pendleton took on Frankie Randall (27-1) for the second time; it was for the vacant USBA lightweight title.
In 1990, Pendleton fought a world title against unified WBC & IBF lightweight champion, Pernell Whitaker (20-1).
Although the outcome was declared as a unanimous decision win for Whitaker, most observers generally thought the fight was much closer than the scorecards reflected (Judges Jim Traylor and Stuart Winston scored it 116-112, with Phil Newman 117-113 all for Pernell Whitaker).
In 1993, Pendleton captured the Vacant IBF lightweight title with a decision win over Tracy Spann.