Weah signed for Premier League club Chelsea on loan from Milan on 11 January 2000, in a deal which would keep him with the West London club until the end of the 1999–2000 English season. Although past his prime, Weah's time in England was deemed a success, especially at Chelsea where he instantly endeared himself to their fans by scoring the winner against rivals Tottenham Hotspur on his debut, and scored further league goals against Wimbledon and Liverpool. He also scored twice in Chelsea's victorious 1999–2000 FA Cup netting crucial goals against Leicester City and Gillingham. This led to him starting in the final, which Chelsea won 1–0.