[6] In 1994, Stelling became presenter of Sports Saturday, which became Gillette 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, Rodney Marsh and George Best.

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.

[8] On 21 November 2008, it was reported that Stelling had been confirmed as the new host of the Channel 4 game show Countdown following the departure of Des O'Connor.

[9] Stelling began recording Countdown in December 2008, with the show's new assistant Rachel Riley, and started broadcasting in January 2009.

Stelling returned to Countdown as a guest in Dictionary Corner in August 2023 and, at the invitation of the host Colin Murray, swapped places to present the final part of the week.

Stelling appears as himself in a number of episodes of the football comedy TV series Ted Lasso.

[14] From 4 December 2023, he started presenting Talksport's breakfast show every Monday and Tuesday (6am to 10am) alongside Ally McCoist.

[19] Stelling was appointed Member of the Order of the British Empire (MBE) in the 2024 New Year Honours for services to sport, broadcasting and charity.

[25] In 2016, Stelling walked 262 miles from Hartlepool United to Wembley Stadium over 10 days raising over £420,000 for Prostate Cancer UK.

He walked with his friend Russ Green, who was the Chief Executive of Hartlepool United at the time, and was joined by over 400 walkers including his friends from Sky Sports and the football world such as Chris Kamara, Matt Le Tissier, Charlie Nicholas and Paul Merson.

[28] In his book, "I've Got Mail"[29] published on 17 September 2020, Stelling revealed he had been subject to a blackmail attempt via two letters sent to his home.