Dean started his footballing career as a trainee at his hometown club, Hull City, and signed his first professional contract there. He scored 64 goals in 205 games for Hull, and, when he left, he brought the club a record transfer fee at the time, going on to play in the top divisions in both English and Scottish football. Later in his career, he returned to Hull City, and scored the only goal of the 2008 Football League Championship play-off final to take them to the top flight for the first time in their history.
Dean also had two spells at Bradford City, where he became the club’s third-highest scorer of all time. He has also played for Aberdeen, Oxford United, Middlesbrough, Sheffield Wednesday, Sheffield United, and Oldham Athletic. He is seen as a controversial player, once being sent off three times in a game for Aberdeen, as well as grabbing another opponent’s testicles in a match at Bradford City but Dean would argue he was just being friendly.
Windass scored his last Premier League goal at the age of 39, becoming Hull City’s oldest-ever scorer. He officially announced his retirement from the game on 19 October 2009. Dean is now an ambassador for Hull City club and works in the media and after dinner circuit.