[3][4] Winton started DJing in clubs in Richmond in 1972, where he met Steve Allen, the LBC radio presenter.

This led him to the United Biscuits Radio Network where he did a variety of jobs working for Adrian Love, before getting his own morning show.

[8][9] In 2000, Winton took over from Alan Freeman to present Pick of the Pops on BBC Radio 2,[10] and hosted the show until 30 October 2010, when Tony Blackburn replaced him.

[11][12] Winton sat in for Steve Wright and Liza Tarbuck on BBC Radio 2, covering the latter's Saturday show in September 2013 and November/December 2016.

Winton portrayed himself as an irritating game show presenter in Danny Boyle's 1996 film Trainspotting.

[2] In 1995–96, Winton presented BBC's Saturday night game show Pets Win Prizes.

[21] In 2003, he appeared in the BBC Three mockumentary, Dale's Wedding, in which he supposedly married the UK celebrity Nell McAndrew.

[27] In a 2016 op-ed for the Conservative Woman website, he revealed his interest in American politics, expressing his disappointment over Mitt Romney's loss of the 2012 US presidential election.

[31] According to his friend Gloria Hunniford: "Dale had a lot of things going wrong, he had pain with arthritis, he had a heart complaint, he had a chest infection, and we all know how the winter affected that.