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.
On January 13, 2000, Bill Gates handed over the CEO position to Steve Ballmer, an old college friend of Gates and employee of the company since 1980, while creating a new position for himself as Chief Software Architect.
At Royal Rumble, on January 23, 2000, The Rock entered the Royal Rumble match and was one of the final two remaining, along with Big Show; In an attempt at a "false finish", Big Show intended to throw The Rock over the top rope in a running powerslam-like position, before The Rock countered the move on the ring apron, sending Big Show to the floor before re-entering the ring as the winner.
On 26 January 2000, the Russian government announced that 1,173 servicemen had been killed in Chechnya since October, more than double the 544 killed reported just 19 days earlier.
On January 26, 2000, an altercation during the filming of the music video for Rage Against the Machine's "Sleep Now in the Fire", directed by Michael Moore, caused the doors of the exchange to be closed and the band to be escorted from the site by security after the members attempted to gain entry into the exchange.
Hazmi and Mihdhar arrived in the United States in mid-January 2000. In early 2000, Hazmi and Mihdhar took flying lessons in San Diego, California, but both spoke little English, performed poorly in flying lessons, and eventually served as secondary – or "muscle" – hijackers.