 Despite Skoff's relative success during his career of winning four top-level tournaments, his memorable Davis Cup moments, and reaching a career high world ranking of 18 in singles competition, he never managed to progress beyond the second round at any Grand Slam event.Skoff played in his last top-level tournament in August 1995, at the San Marino Open.From 1996–1999, due to his lower world ranking, Skoff played in challenger and futures tournaments.