Debt, delays & desperation - how Sheff Wed crisis impacts fans
But in the years since losing that final, Chansiri's reputation and supporters' morale have taken a steady hammering.
Late payments to HMRC, delayed salaries for players and staff members, and transfer embargos have clipped the club's wings.
There were concerns about whether their first match of the season against Leicester on Sunday would go ahead, but it is understood the players will fulfil the fixture.
Now, with a skeleton squad, enforced stand closure and dire financial prospects, fans have told the BBC what they feel Chansiri's failure to sell is doing to the club, the city, and its people.
"We're all struggling," says Hillsborough season ticket-holder Gaz Robinson. "It's been terrible for everybody - mentally exhausting.
"We need the chairman to see sense, to take into account how we feel, how the city is feeling, and make the right decision."
Sheff Wed players to fulfil Leicester opener
No manager, unpaid wages and a closed stand - Sheffield Wednesday latest
In Chansiri's early years in charge following his 2015 takeover, Wednesday spent heavily as they targeted a return to the Premier League for the first time since 2000.
But in the 2020s the level of spending has receded significantly, debts and creditors have risen sharply, and though Chansiri has indicated he is open to selling the club, no takeover has materialised.
That has led to fans worrying they might not have a club left to support if things do not change soon.
"Absolutely everything has gone wrong," says Natalie Briggs, who has been landlady of The Park pub - a few minutes' walk from the stadium - for 10 years.
"Twelve months ago some people were still 50/50 about whether he [Chansiri] should stay or go. But now it's got to a stage where everyone wants him gone.
"He claims to be a family man, yet he can't see that he is destroying the biggest family of all - the family that he bought into. He made that decision. And where is he now? Nowhere to be seen.
"We're the ones still here. We're standing up. We're shouting for our players. We're backing them 100%. And he's just run off like a rat from a sinking ship."
The impact of the crisis on those who have followed the club for decades is stark, and fans are determined to face Chansiri head-on.
"There have been bad times before, but this is certainly the worst in my life," says 84-year-old retired ambulance driver Bill Button, who first went to a match at Hillsborough 79 years ago.
"It's doing my head in. I just don't know where Chansiri is coming from. We won't buy a new shirt for the simple reason that the money is going in his pocket. You've got to hit his pocket. If not, it won't make any difference."
Button's season ticket is located in the disabled section of Hillsborough's North Stand, which has now been closed after the Safety Advisory Group refused to renew its safety certificate until renovation work is undertaken.
The club has not provided Bill with any information about what is happening with his season ticket.
"I've rung up many times and just get hold music," he says. "They can't even give you an answer for anything.
"I'm really fed up with it. I get really low, feeling really down. It's not good for me at all. Anybody that knows me knows that going to Wednesday is all that I am. I'm just at my wits' end."
While fans' anger is primarily directed at Chansiri, some are frustrated the club has not been protected from one man's decision-making by the English Football League (EFL), whose owners' and directors' test Chansiri passed in 2015.
"What we've seen from the EFL is nothing," says fan Ryan Goodison. "And we're not alone in that. Look at what has happened at Morecambe.
"I think Chansiri would rather see no Sheffield Wednesday than Sheffield Wednesday without him, and I don't know what the EFL can and can't do because obviously it's a private business. But if there is nothing they can do, then what is the point?
"I'm 40 and been coming to Hillsborough since I was five. For that to suddenly be possibly taken away is awful."
The EFL's measures for assessing potential owners' credibility have been amended since Chansiri bought Sheffield Wednesday, but are based on whether individuals are able to provide proof of funds at the point of purchase, rather than whether owners can continue to fund their clubs throughout their tenure.
The incoming Independent Football Regulator (IFR) will have the power to potentially revoke operating licenses from club owners during their tenure in some circumstances.
This summer, Chansiri claimed he had turned down two potential bids for the club worth £30m and £40m.
Fans who spoke to the BBC said they believe the 57-year-old's valuation of the club is too high, and insisted they will protest against him inside and away from stadiums for the foreseeable future.
Supporters are planning to demonstrate their disapproval by only entering the away end at Leicester City for Sunday's opening fixture once the first five minutes have passed.
"We are going to be protesting in our own way," Robinson says. "The atmosphere is going to be toxic.
"But we all have jobs and we don't want a criminal record so we need to act appropriately. We have to show that we are above some things and have more respect than the owner has for us.
"This is our everything - to him it's a plaything. We have to show him that his time is up, that we don't want or need him any more, and that he needs to leave."
Whether Chansiri will seal his own exit in time to avoid a likely points deduction, a descent down the divisions, and further misery for fans, remains unclear.
Sheffield Wednesday, Dejphon Chansiri, and the EFL declined to comment when asked to do so by the BBC.
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