Premier League Career: Bradford City (1999-2001), Middlesbrough (2001-2002), Hull City (2008)
In November 2008, Dean Windass became one of the oldest goalscorers in the history of the Premier League when his scrambled equaliser earned his hometown club, Hull City a 2-2 draw away at Fratton Park against Portsmouth. He was 39 at the time, becoming the Tigers’ oldest-ever scorer in the process. He is back at Hull now, working as a Club Ambassador which he has held since 2015.
It was a career that went full circle. He started his career at Hull, signing his first professional contract in 1991 at the relatively late age of 22. Previously, he had been playing at part-time level for North Ferriby United whilst holding down jobs packing frozen peas and working on building sites. With the club in financial difficulty and after scoring 64 goals in 205 games, he was sold to Aberdeen for £700,000 in December 1995.
He became a fans’ favourite at Pittodrie but a fiery temperament was always part of his game and none more so than in a league game in November 1997 against Dundee United. Incredibly, he was sent off three times in the same match! The reasons were foul play, abusing an official and kicking the corner flag as he left the pitch. He received a six-game ban from the authorities. He moved to Oxford United in the summer of 1998, scoring 15 times for them before being transferred again, this time to Bradford City in March 1999 as Paul Jewell seeked a final boost to his attacking line-up ahead of a promotion bid to the Premier League.
Windass scored twice in 12 matches including a goal in a crucial away win at Bury as Bradford won promotion as runners-up in the First Division. Rather than go on holiday, he decided to train all summer, preparing for his debut bow in the Premier League. He finished as the Bantams top goalscorer in 1999-2000, finding the target 10 times including a Good Friday hat-trick in a 4-4 thriller with Derby County. Bradford beat the odds and avoided relegation on the final day of the season.
In March 2001, he was sold to Middlesbrough for £600,000 but only made 38 first-team appearances for the club which included loan spells at both Sheffield clubs during his spell on Teeside. Sheffield United turned his loan into a permanent transfer but after being dropped by Neil Warnock for the play-off final defeat to Wolverhampton Wanderers, he elected to return to Bradford for a second spell at Valley Parade.
Bradford’s fortunes had nosedived dramatically as they struggled financially but Windass enjoyed arguably the best spell of his career in terms of goals. He ended up as top goalscorer in League One in 2004-2005, with 27 goals in 41 matches and ended as the club’s third highest all-time goalscorer before rejoining Hull in 2007.
In 2007-2008, he helped shoot Hull to a surprise promotion to the top-flight, scoring 11 times in 37 appearances. During that season, he made his 700th career appearance and scored his 200th goal in English football. The fairytale concluded with a spectacular winning strike in the play-off final victory over Bristol City which secured the Tigers promotion to the top-flight for the first time in their 104-year history.
The goal at Fratton Park was one of his final Premier League contributions. In total, he played just five times in the top-flight and was allowed to leave in January 2009 to join Oldham Athletic. He finished his professional career later that year, briefly working afterwards in the player-coach capacity at Darlington. He has hoped to get into management but made unsuccessful applications for managerial positions at Grimsby Town, Shrewsbury Town and Hartlepool United. Alongside his ambassadorial commitments with Hull, he is also overseeing the development of his son Josh, who currently plays for SkyBet EFL Championship side Wigan Athletic after a spell in Scotland with Rangers.