Winton began his television career in 1987, working for Channel Four, the Lifestyle Channel and ITV. From 1993 to 2001, Winton hosted Dale's Supermarket Sweep during the Daytime TV period on ITV1. In 2007, Supermarket Sweep was revived after a five and a half year absence. Winton was seen as the camp, over-the-top, game show presenter in Danny Boyle's 1996 film of Irvine Welsh's 1993 novel Trainspotting, in 1995 and 1996, Dale presented the Saturday night game show Pets Win Prizes.

In 1997, he presented the final of The Great British Song Contest, the UK's national pre-selection for the Eurovision Song Contest, due to a tie-in with the lottery programme.

In 1999 he appeared on the sitcom Gimme Gimme Gimme with Kathy Burke in the episode Do They Take Sugar?

In 2000 Dale took over from Alan Freeman to present Pick of the Pops on BBC Radio 2, and hosted the show until October 30, 2010, after that date Tony Blackburn replaced him.

Dale has also sat in for Steve Wright on BBC Radio 2, most recently for 3 weeks in July 2010.

In 2001 he presented Channel 5's endurance show Touch The Truck.

In 2002 he released his autobiography in which he wrote about his rise to fame, his actress mother's suicide and came out about his homosexuality.

In 2003 he appeared in the BBC Three mock documentary “Dale's Wedding” in which he supposedly married the UK celebrity Nell McAndrew.

Between 2004 and 2006, he presented three series of the celebrity weight loss “boot camp” programme, Celebrity Fit Club on ITV1.

In April 2006, he guest presented BBC Two's pop quiz Never Mind the Buzzcocks.

In August 2006 he was chosen to host the pilot of Endemol's new show, Show Me What You've Got, however the show did not receive a full series.

In 2008, he continued to host the BBC One primetime Saturday night game show In It To Win It.¹⁰ In February 2009, he signed a new contract to host at least two further series of the show, plus two series of a new Lotto tie-in.

In February 2008 he completed a pilot show for BBC One called You've Got The Answer, a money game show that surprises the public using hidden cameras.

In 2008 Winton presented BBC One's Saturday night entertainment programme Hole In The Wall, based on the Japanese original, where contestants in skin-tight Lycra costumes contort themselves to fit through oddly-shaped holes in a moving wall.

In 2010 Winton began appearing in television advertisements for cashmygold.co.uk.

Winton appeared on Matt Lucas and David Walliams new comedy show Come Fly with Me (2010 TV series) he appeared in the last episode playing himself.