He went to Rift House Primary School and to West Hartlepool grammar School. When he finished his high school, the first job he had was working like a journalist from Hartlepool Mail where he worked for over four years. The first broadcasting position was when he worked as a reporter of Middleborough F.C on the Radio Tees in the 1970s. He was the sports presenter in LBC Radio Sportswatch program in London. This is before moving to BBC Radio 2 for the Sport On 2 and he was covering the Seoul and Los Angeles Olympic games.
This is before moving to the Sky in the year 1992 where he was in charge of covering darts, snooker and horse racing. In the year 2003, he won the sports presenter special edition for The Weakest Link. In the year 2004, Stelling was given and also rejected the offer of BBC for the Front Score. In the year 1994, Stelling started to present Sports Saturday and it became the Gillette Soccer Saturday in the year 1998. He was hosting the program that lasted around six hours for the football discussion and he was live reporting the games of afternoons. He was working with the panel of pundits like late George Best, Rodney Marsh, Chris Kamara and Frank McLintock. He was one behind the popularity of the program and the guardian praised him for his exceptional professional with Elan.
In 2011, Stelling replaced the departed Richard Keys as the main presenter of Sky's live Champions League coverage and hosted between 2011 and 2015.