Stelling was brought up in the North-East town of Hartlepool and is a supporter of local team Hartlepool United. After an apprenticeship on the local newspaper, his first broadcasting position was as a reporter on Middlesbrough F.C. for Radio Tees before moving to BBC Radio 2's weekend sports programme Sport on 2, covering the Los Angeles and Seoul Olympic games. He later spent time as a sports newsreader at TV-am, Channel 4, Eurosport and British Satellite Broadcasting before moving to Sky in 1992 to present coverage of horse racing, snooker and darts.
In 1994, Stelling became presenter of Sports Saturday, which became Soccer Saturday in 1998, hosting a programme lasting up to six hours of football discussion and live reports on the afternoon's games with a panel of pundits including Frank McLintock, Chris Kamara and Rodney Marsh. Much of the programme's popularity is put down to Stelling, The Guardian praising him for “exceptional professionalism” and When Saturday Comes describing him as "perhaps the best sports presenter on British TV".