Dempsey made the Fulham XI only once in the first eleven fixtures of the 2008–09 season but scored his first goal in a 1–1 away draw at Portsmouth on October 26 after coming on as a substitute. He replaced Zoltan Gera in the side and scored his first home goal of the season in a 3–0 win over Middlesbrough on December 20. Eight days later he scored twice in the West London derby against Chelsea which included a last-minute equalizer in a 2–2 home draw.