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After graduation, he spent a year producing a magazine on sport in London. He then joined The Independent newspaper at its launch, writing a sports and schools column. Winter moved to The Daily Telegraph in 1994. During the 2006 FIFA World Cup in Germany, he gave a daily webcast on the World Cup in general, with specific information on the England team. Winter often takes part in television discussions, including Sky Sports Sunday Supplement, and radio including BBC Radio 5 Live.
Winter formerly wrote a column for Four Four Two magazine. He ghost-wrote the autobiographies of Liverpool FC players Kenny Dalglish, John Barnes and Steven Gerrard. Winter also co-wrote the book FA Confidential with former FA Chief Executive David Davies. He is a trustee of the African social enterprise Alive & Kicking, which manufactures footballs in Kenya and Zambia.
In 2012 Winter was named among the top 10 most influential sportswriters in Britain by the trade publication, UK Press Gazette. 
Winter is an Arsenal fan.
- Interview with older brother Tim Winter in the Independent
- Paul Bestall (5 October 2009). "EPL Talk Meets Henry Winter". EPLTalk.com. Retrieved 28 June 2010.
- Eriksson hammered by British media CNN, (July 3, 2006).
- Henry Winter misuses 'enervated again!
- In 2012 Samuel was named top in a UK Press Gazette poll of Britain's best sports journalists.
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