To every Hull City fan, 24th May 2008 is the day that will live in memory as the biggest day in the club’s history - the day they were promoted to the Premier League for the first time. 

Dean Windass - the hometown boy in his second spell at the club - secured the achievement with a thunderous volley which announced the Tigers ascendancy onto the big stage. Twelve years later, the club are staring down the barrel of relegation to the third tier of English football for the first time since 2005. 

  • Dark days of Boothferry Park

Ten years previous to the clubs promotion to the Premier League, Hull City came close to going out of existence. Under the stewardship of Martin Fish, David Lloyd and then Steven Hinchcliffe and Nick Buchanan, the club were in administration and had experienced very dark days indeed in the mid to late 1990s. Only under Warren Joyce in the so-called “Great Escape” season of 1998/99 was there any rest bite, and it was only when Adam Pearson came to buy the club in 2001 that Hull fans had any reason to be hopeful again.

Now with money to spend, the sleeping giant of a club reached the play-offs during Brian Little’s managerial reign, losing to Leyton Orient in the semi finals in the 2001/02 season.   Striker Rodney Rowe remembers those days with bittersweet memories. The former Hull City striker spoke to a Hull City podcast over lockdown and to this day  still regrets that the team did not achieve promotion against all the odds. 

  • Rowe: "We shouldn't have failed"

Rowe told Tigers Tigers Blah Blah Blah Podcast, "We put ourselves in that position (being able to make the play-off final), and we still failed. We shouldn't have failed. I would have loved to have given - not just myself - I wish the players at the time could have given those fans that.

"Even if we'd have got to Wembley and lost, it would never have mattered to me, because if you think of what we went through in that season, you couldn't have criticized us as players. No-one could have had a go at us. Nobody."

Ultimately, Little paid the price for falling at the  final hurdle in that season - he was sacked not long into the 2002/03 season. Jan Molby came in, and again didn’t achieve what the ambitious new owner Pearson wanted in getting anywhere near promotion at the first time of asking. The money was spent; the results did not follow. 

Peter Taylor came in, and the rest, as they say, is history. Back to back promotions in 2003/04 and 2004/05 seasons, and then the club consolidated in the Championship the season after. The club had gone from the old Division Three - now dubbed ‘League Two’ - into the Championship and survived in three seasons.

  • Fagan - "The away support was unbelievable"

Current Southend United Under 23's Manager Craig Fagan remembered the good times of those seasons under Taylor, saying just how much the fans and the players had an affinity with each other. He spoke of the club's support during the season he joined - 2004/05 - to Tigers Tigers Podcast, and particularly touched on the demand for games to be "beamed back" to the home stadium for fans to watch when the away allocations were snapped up.

"I'd never heard of it beamed back to a football club before", he said. "I couldn't believe it. The amount of people that came to games - the away support was unbelievable. But then we were still having all that support at home! I couldn't believe the amount of people going to watch at that time, it was surreal".

Dwindling numbers in stadiums, then - which has been a problem in the last few years - was never Hull City's problem in the mid noughties. 

Despite a disastrous start in 2006/07 under Phil Parkinson, Phil Brown guided the Tigers to Championship safety on the last day of that season - with the acquisition of Dean Windass being instrumental in that. The forward scored in the 1-1 draw with Cardiff City that kept the Tigers in the division. The good times were on their way - although not many thought so at the time.

  • Pearson out, Duffen in: Premier League push

Safety for the club meant new owners, with Paul Duffen - together with a consortium with Russell Bartlett - bought the club for a reported £13 million from Adam Pearson. Money was promised to invest in the squad, and so it came. Caleb Folan - very outspoken about the state of the club in recent weeks after the defeat to Wigan Athletic - came in as the first million pound player, along with big games like Jay Jay Okocha, Henrik Pedersen and eventually Fraizer Campbell on loan from Manchester United. Campbell was a player City coveted for many seasons after, but did finally return to the club between 2017-19.

The club was now ambitious - much more ambitious than it ever had been before. Pearson had always spent the money and backed his managers, but Duffen and his consortium seemed to be taking the Tigers to the next level, which was exciting for the fans who less than ten years before had almost seen their club disappear.

  • Folan: "The spirt was always at a high"

Caleb Folan was also a guest on Tigers Tigers Podcast over lockdown, and had fond memories of his time at Hull City, particularly in the promotion season.

"I remember nothing feeling negative, it was always a positive mindset," he said. "We found ourselves in the play-offs, and it was always led by a positive. The spirit was always at a high, it was never at a point of dipping".

The contrast between this Hull City and the team currently bottom of the Championship could not be further removed.

The 2007/08 surpassed any Hull City’s wildest dreams, with Phil Brown - appointed as permanent boss by Duffen - guiding them to the promised land of the Premier League. The goal by Dean Windass is perhaps one of the most iconic images in football - and it was indeed redemption for Windass. Sold back in the mid-nineties to Oxford United just to keep the club afloat financially, it was written in the stars that the lad from Gipsyville Estate in Hull would be the one to fire them into the Premier League. 

  • The Tigers get up, and stay up

A mixture of experience and youth proved to be the perfect storm and the Tigers not only went up, but stayed up on the final day of the season. Big money signings like Giovanni and George Boateng drew the headlines, but ultimately it was Craig Fagan who scored the goal away at Bolton Wanderers to keep the Tigers in the Premier League for a second season.

They had a torrid time in the second half of the season, picking up only nine points in the period from the start of 2009 to the end of the season. Perhaps many could compare this campaign to the current season in terms of form, but the difference was that the Tigers of 2008/09 could dig in when it mattered. There were leaders on the pitch and the determination to survive in a league where people had written them off. The leaders - or lack of leaders - in the 2019/20 squad is very apparent to even the most casual observer.

  • Back down to the Championship - the consolidation years

Second season syndrome proved to be too much for the Tigers, as they dropped back down into the Championship in the 2009/10 season. Duffen was also gone, as well as Phil Brown - Iain Dowie came in but couldn’t keep the club up. The club in dire financial straits yet again and Adam Pearson came back for his second spell at the club. 

Nigel Pearson was the next manager, and under tough financial circumstances did an excellent job to consolidate the club in the Championship once again. It was during this time that Chairman Assem Allam came into the club. 

  • Enter Assem Allam - Started well, but went downhill

After a very positive start to his ownership of the club - marred possibly by the sacking of Nick Barmby as manager for reportedly criticising the owners on local radio - the appointment of Steve Bruce proved to be an astute one. The start of the 2012/13 season brought much optimism, and this yielded the ultimate reward - promotion back to the Premier League as runners up in the division. However, it was here that the trouble started, and why Hull City are in the mess they are today. 

The proposed name change to “Hull Tigers” brought about much resistance from fans. However, it wasn’t only the fans who the Allams failed to convince - it was also Hull City Council, with the owners being told they could not buy the stadium to develop as they wished.

On the pitch, successes kept coming. The club not only stayed up in the 2013/14 season, but got to an FA Cup final and qualified for the Europa League for the first time in the club’s history. The second season back in the top flight again proved too much for the Tigers. They recruited big names yet again, but Bruce failed to get a tune out of the squad and they went down back to the Championship. 

Bruce guided them back to the Premier League in the 2015/16 season, this time through the play-offs against Sheffield Wednesday. There was talk of a new buyer coming in at this time, but this failed to materialize. The Athletics’s Adam Crafton recently wrote about the alleged meetings in an in depth piece on Hull City, and in truth the promotion to the Premier League should have been a return to the good times. However, it was more like the beginning of the end for the club in many supporters’ eyes. 

  • The start of the decline

Steve Bruce resigned weeks before the season started. The club was left with only 13 full time professionals at the club. Mike Phelan took over but the club struggled after a good start. Marco Silva was brought in at the turn of 2017 to try and save the club - but ultimately failed. Some players - Andy Robertson, Harry Maguire - went on after Hull City to have very successful careers, which showed that in some instances, the recruitment was spot on. In other areas though, the club was woefully misguided. 

Fans were starting to stay away from the club. Not only those against the name change, but the owners scrapped the concessions at the club, making it expensive for families to go to games. The rebranding of the club’s badge in previous seasons also irked many - “Hull City” was no longer on the badge. Instead, there was simply a tiger with “1904” on it, the year the club was formed. Many felt this was an act of deliberate petulance from the owners, as the chants Hull fans sang in protest of the Allams’ name change (rejected by the FA) rang, “We are Hull City - since 1904”. The badge has since been changed to resemble the previous versions of it, but it seems that the damage was already done in supporters' eyes.

  • Did previous good recruitment paper over the ever widening cracks?

Leonid Slutsky and Nigel Adkins have come and gone from the club since 2017. Hull still had very good players at Championship level - Abel Hernandez, Kamil Grosicki and Jarrod Bowen to name but a few. It seems that the aforementioned players - Grosicki and Bowen - masked a lot of the Tigers’ problems in recent seasons. This can be confirmed when we look at where Hull City were in the table on New Year’s Day under current boss Grant McCann. 

After defeating Sheffield Wednesday 1-0 on 1st January, Hull have picked up six points in 2020. Their only win since came at the start of July against Middlesbrough, and the club have gone from eighth to 24th in the space of nineteen games. Their defensive frailties have been there for all to see, but their manager has been stubborn with his formation and played a system that does not necessarily suit his players. 

In that time, they have waved goodbye to key players and experienced their worst defeat in 109 years. Grant McCann is still in his post, and it does not look like he is going anywhere soon. The same can be said for Ehab Allam, Assem Allam's son and current owner. 

  • What does the future hold for the Tigers?

How can it have come to this? From the brink of extinction around the turn of the century; to Premier League regulars, to League One mediocrity next season? There are obviously a whole host of factors to the current situation at the KCOM Stadium. The owners seem to be at the center of this - alienating the fan base, stripping assets, even banning local media from home games for so-called "negative" reporting.

One thing is clear - the day the current owners sell up is the day that the vast majority of Hull City fans will rejoice and flock back to their beloved club. Until then, a dark future awaits the club as they currently sit in limbo, waiting for the trap door of relegation to open to drop them back into League One for the first time in fifteen years.