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In May 2018, Winkleman co-presented The Biggest Weekend on BBC Two and BBC Radio 2.In 2018, she starred in a TV commercial for Procter & Gamble's Head & Shoulders Suprême premium shampoos and conditioners designed for women.She shared the presenting duties with Colin Paterson, and later Paddy O'Connell. In 2003, Fame Academy appointed Winkleman to present a daily update show on BBC Three, in conjunction with its second series.She repeated the show in 2005 for the much shorter celebrity version Comic Relief Does Fame Academy.Winkleman was also the presenter of Film..., replacing Jonathan Ross after his move to ITV in 2010.
In 1992, she began frequently appearing in the long-running BBC series Holiday, and this continued throughout the mid-1990s.
Winkleman then presented several more reality shows including End of Story, More recently, Winkleman has presented a number of prime time programmes.
In 2007, she took over from Cat Deeley as the main host for the third series of Comic Relief Does Fame Academy, co-hosting with Patrick Kielty.
On 14 November 2009, she appeared on the main show of Strictly Come Dancing to present backstage, due to main presenter Bruce Forsyth being on sick leave.
She co-hosted the show with Tess Daly and guest presenter Ronnie Corbett.