Early on, Shepherd scored wins over Florida cult legends Gator Garland, Bill Clarke, Harold "Nature Boy" Roth (a.k.a. Harold Diamond), and Joe Marciano. Six months later, in a bout broadcast over CBS-TV, he lost the title in a split decision to Earnest Hart, Jr. He rebounded in 1979, defeating Chris Gallegos for the
WKA middleweight world title (at 160 pounds), and then became the first champion to unify the sport's two major crowns with a sixth-round knockout of Hart to regain the PKA welterweight world title. He was retroactively recognized as the undisputed
STAR ratings world champion upon its founding in 1980. A few months later, Earnest Hart won Shepherd's involuntarily vacated title; Hart was the same contender Shepherd had just knocked out for a second time. a feat that made him the first middleweight kickboxer ever ranked number-one in the heavyweight division. He was also recognized as “Fighter of the Year” by
Official Karate magazine's 1982 Kickboxing Hall of Fame. Moncayo also prevailed in the rubber match when Shepherd again sustained a broken jaw. One year later, in 1983, Shepherd moved up in weight to capture the WKA super middleweight world title from Japan's Yasuo Tabata in a close split decision. In a 1987 retirement interview, Shepherd told South Florida's
Sun-Sentinel newspaper that his biggest fight purse was $45,000.00 and his smallest was $150.00. ==Professional kickboxing record==