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 SportsSunday Supplement, and radio including BBC Radio 5 Live.