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.

In 2012 he began playing for AFC Walkington in the Premier Division of the East Riding League, where his ex-teammate Leigh Palin is the manager.

[11] He was brought back to Hull City by manager Terry Dolan in October 1991, entering professional league football at the relatively late age of 22.

On 9 November 1997, during a league game with Dundee United, Windass was shown three red cards – once for foul play (having previously been booked); another for verbally abusing the referee; and a third for taking out his frustration on a corner flag as he left the field – for which he received a six-match ban.

He transferred to Bradford City in March 1999 for an initial fee of £950,000 as manager Paul Jewell looked to build his squad for a promotion push to reach the Premiership.

[10] His dedication was rewarded as he was the club's top scorer in their first season in the Premiership with ten goals, including a hat-trick in a 4–4 draw with Derby County.

Hutchings was given money by chairman Geoffrey Richmond to spend on new players, which included new strikers Benito Carbone and Ashley Ward.

Windass helped the Blades to the play-offs but he was dropped by manager Neil Warnock for the final, opting instead to watch his side's 3–0 defeat by Wolves in a pub.

Windass remained a controversial character and in September 2006, on FIFA Fair Play Day, he was accused of grabbing fellow professional John Finnigan by the testicles during Bradford City's 2–1 win over Cheltenham Town.

This left Hull City three points ahead of Leeds United with a vastly superior goal difference, meaning virtually certain Championship survival.

[26][27] At the end of the season, the two clubs entered protracted negotiations over the size of the transfer fee required to make the loan move a permanent one.

On 19 June 2007, the transfer was completed, and Windass signed for Hull City on a two-year deal for an initial fee of £150,000, plus further add-ons based on appearances.

[28] In October 2007, Windass' autobiography was published by Great Northern Books, entitled Deano – From Gipsyville to the Premiership, with a foreword from Bryan Robson.

He had predicted scoring the goal several weeks earlier: "When Phil Brown left me out against Sheffield United this year, I weren't [sic] happy about it.

After he was left out of the squad to face Everton on 21 September 2008, he held talks with manager Phil Brown,[41] following which he vowed to stay and fight for his place.

[45] Windass had to wait till 22 November 2008 to make another Premier League appearance for City, coming on as a substitute against Portsmouth with Hull trailing 2–1.

Windass claimed the goal that earned Hull City a draw, with a header from a corner that deflected off defender Noé Pamarot and into the net.

[49] Disappointed by his lack of first team opportunities, Windass was allowed to leave Hull, and, on 9 January, he joined Oldham Athletic on loan for the rest of the season.

[55] After playing just ten times for Oldham, Windass declared on his online blog that he wanted to leave, after a disagreement with manager John Sheridan about his lack of involvement in two consecutive games.

[60] Windass was reported to be close to being named as player–assistant manager at Darlington to recently-appointed Colin Todd, whom he had previously played under during his second spell at Bradford City.

[63] He made his Darlington debut in a 3–1 defeat to Aldershot Town,[64] and a day later he played his Hull City testimonial match against Aberdeen at the KC Stadium.

[citation needed] In August 2010, Windass came out of his retirement to sign for the North Lincolnshire semi-professional side Barton Town, managed by his former teammate Dave Anderson, on a game-by-game deal.

The local press reported that approximately 25 other applications have been received for the post, including from the club's all-time longest serving player, John McDermott.