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Dougherty was born in Salford, Greater Manchester and educated at Stockport Grammar School. She then went to the University of Newcastle upon Tyne, where she studied German. While at university she played golf and netball.
Dougherty's media career began when she joined Galaxy Radio as part of their ground crew. She later joined Sky Sports as a runner before becoming one of the presenters on the Sky Sports News channel. In 2007, Sky launched a dedicated golf programme and Stewart was selected to be one the show's host presenters.
Dougherty has also appeared on other programmes, including Sky3's More Big Ideas, which is shown after the Sky1 show The Big Idea, in which she speaks to the winner and losers of the show. In May 2009, she appeared in a series of adverts for Titleist golf balls alongside ESPN's Scott Van Pelt.
Dougherty is a big golf fan. She first picked a set of clubs at the age of six and was soon representing Cheshire Girls' and Cheshire Ladies' teams. At 17 years old she had a handicap of 6. She played in the amateur teams during the Dunhill Links Championship in 2005. She also appeared in several Titleist TV ads with ESPN's Scott Van Pelt.
Dougherty is a former girlfriend of England rugby player Jonny Wilkinson. She married European Tour golfer, Nick Dougherty on New Year's Eve 2010, She had a baby boy in August 2012 called Maximilian James. Di is back on Sky Sports from August 2013 presenting a show every Saturday morning with Darren Campbell called Game Changers.
- Moncur, James (7 January 2011). "Royals head to Scotland for secret wedding as TV presenter Di Stewart weds golfer Nick Dougherty". Daily Record. Retrieved 2011-02-18.