In 1993, Wilson joined Sky News as a reporter. He reported from Bosnia, the Middle East, across Europe, Africa and in Perth, Australia. In 1998, he became Sky News Moscow Correspondent, covering the war in Chechnya. He was also part of the award-winning Sky News team that advanced in 1999 from Macedonia into Kosovo alongside the KFOR troops, and he reported on Boris Yeltsin's resignation on Millennium night. In January 2001, he became Sky News Middle East Correspondent, based in Jerusalem, and was with the first wave of Western reporters to cross overland into Kabul in 2001. He became Sky News US Correspondent in 2004, reporting from locations across the United States on the run-up to, and outcome of, the US Presidential Election. In December 2004, on special assignment to South East Asia, he fronted Sky news coverage in Thailand of the aftermath of the Indian Ocean earthquake and tsunami, and in 2005 reported live on the destructive power of Hurricane Katrina from a Mississippi motel room.