After an unsuccessful YTS placement with City, 'Deano' combined work as a 'brickie' with playing local football before attracting the attention with impressive displays for North Ferriby. One such display, against the Tigers in a pre-season friendly, convinced Terry Dolan that Windass could make it in the League game and he was signed by the club for a second time in October 1991. Playing initially in midfield, his enthusiasm, skill and bellicose style of play marked him out as a quality player and he quickly became a firm favourite with the fans. When he was pushed up into the attack, his goals made him a priceless asset. It was an asset that would inevitably have to be realised but at least in the interim, City fans could enjoy watching it grow in value and stature.
Instinctively confident, he would blend simple touches with complex footwork and distribution. They were qualities based essentially on a speed of thought that bemused opponents and gained him the reputation as an imaginative and inspiring player. His goals came in all guises: long range strikes, gentle tap-ins and ingenious free kicks. He was almost the finished article and, as such, to retain his services was becoming increasingly difficult.
When he did leave due to the club's desperate financial state his skills were exported to Aberdeen and he captivated the Dons' fans just as he had done City's. It was a spell, however, when the Dons were shackled by the need to recapture former glories and an almost continuous fight against relegation. It was also a spell when he gained the interesting achievement of receiving three red cards in one game. But then again 'Deano' never did anything half-heartedly!
After two and a half seasons he returned to the English game, initially with Oxford, before assisting Bradford City to promotion in the 98/99 season. This meant he would be able to test his skill at the highest level in the Premiership and whilst the Bantams struggled, Windass passed his test with flying colours, ending the season as their top scorer and playing a vital role in ensuring that the Bantams held on to their top flight status.
Windass departed for Middlesborough during the 2000/01 season and played a part in securing their Premiership status under Terry Venables. However, the arrival of ex-Tiger Steve McLaren as Manager limited his first team chances and he went on loan spells to both Sheffield Wednesday and United, and soon after joined the Blades on a free transfer. He helped Neil Warnock's side into the play-offs, but fell out with the boss when he was dropped for the final and returned to Bradford on a free transfer. The Bantams were falling from grace and in Deano's first season back at Valley Parade the side suffered relegation to League One. He proved that he still knew where the goal was in that division, scoring 55 goals over the next 2½ seasons. Bradford even turned down a reported £500,000 offer from Premiership side Wigan during that time, and it looked as though Windass would end his career with the team he had made his most appearances for. But when Hull City came calling in January 2007, Deano couldn't resist his Tigers swansong. Bradford, suffering from financial difficulties, and Hull City, now managed by Phil Brown after previous managers opposed the idea of signing Windass, agreed a one-off fee and terms to see the 37-year-old move on loan for the remainder of the season. His 8 goals in 15 league starts left him as the top scorer for 2006/07, the last of those goals being the winner away to Cardiff that effectively secured the Tigers' place in the Championship for another year. That persuaded the club to shell out £150,000 to bring the 38-year-old back to Hull on a permanent basis, now wearing the number 9 shirt.
Windass again proved to be a key player in 2007/08, finishing as joint top scorer with 15 goals and regularly keeping record signing Caleb Folan out of the starting eleven. Phil Brown's faith in 39-year-old Windass paid off when he scored a stunning volley at Wembley against Bristol City - the only goal of the 2008 Championship play-off final. It sent Deano's hometown club up to the Premier League for the first time in its 104-year history.
He could have walked out then, never needing to pay for his own drink in Hull again, but he was determined to keep playing for as long as he could and where better to do that than with his hometown club in the Premier League. To Deano's disappointment, he didn't get to do that very often. He started the 2008/09 season on the bench and before long was struggling to get even that close to the side, and in his own weekly column on the ITV website he had a platform to vent his frustrations publicly.
Windass claimed a Premier League goal by getting the slightest of touches on the last minute equaliser away to Portsmouth having come on as a substitute. The following week he came close to outdoing his triple-sending off by getting booked... without even being on the pitch. As Stoke's Rory Delap prepared one of his famous long throw-ins, substitute Deano warmed up suspiciously close to him and was shown a yellow card for his antics. More frustration for Windass as Phil Brown now wouldn't bring him on and risk him getting a second.
His last appearance in a City shirt was in his only Premier League start for the club. 4-0 down away to Manchester City, Brown infamously conducted his half time teamtalk on the pitch, which Windass wouldn't see any more of after being substitued. Feeling the "scapegoat", Windass took the chance to go out on loan to Oldham Athletic. It was supposed to be for the rest of the season, but after 1 goal in 11 games - one of which was spent mostly in goal where Deano even faced a penalty and yet kept a clean sheet - he was complaining again about not being in the starting line-up and the deal was terminated.
With his Hull City contract at an end, he re-united with former Bradford boss Colin Todd to become his assistant manager at Darlington.