The father-of-two has struggled to adjust to life since quitting football two years ago and says he has cried every day.
Last year he split from Helen, his police officer wife of 18 years, after she found out he had been seeing a girl he’d met in a pub behind her back.
And just a few days ago, following the sudden death of his father, Dean attempted to take an overdose of pills.
Luckily a former girlfriend turned up at his door in the nick of time and, realising what he had done, forced him to drink pints of water until he was sick.
But the following day after slipping back into the grips of depression and drinking half a bottle of strong amaretto liqueur, he tried to commit suicide again.
At the height of his fame Windass was earning more than half a million pounds a year.
In 2008 he scored the goal that would take his home town club Hull into the top flight of English football for the first time in their 104-year history.
He also appeared in the Premier League for Bradford City and Middlesbrough and played in the Scottish Premier League with Aberdeen before ending his professional career, which spanned 19 seasons, in 2010.
Loved by the fans for his passion on the pitch, with a beautiful wife and loving family it seemed he had it all.
But after squandering most of his fortune on clothes and top-of-the-range cars Windass has been left almost bankrupt, unable even to pay for his son’s car insurance.
After retiring from playing Dean had hoped to move into management. But things didn’t work out and he found it impossible to get work.
Without the day to day routine that football had provided for so many years he quickly spiralled into a self-destructive lifestyle, filling most of his days with trips to the pub.
And with his reputation as a local hero, fellow drinkers were only too eager to keep buying him pints.
Windass, who at 42 is the same age as Gary Speed, told The People newspaper of his troubles which include the breakup of his 18-year marriage, drinking and financial worries.
He said: ‘People outside football think we have it all. But I was in a hole that I honestly didn’t know how to get out of.
‘Just over a week ago I hit rock bottom and decided to end it all.
‘I first took an overdose and when that didn’t work tried to hang myself. I felt so alone and believed I had nothing to live for.
‘I need to sort myself out which is why I’m speaking out now. It’s part of me getting better – part of the healing process.
‘People have this image of me as this big strong man who can take anything life throws at him. But I’m not ashamed to say I wanted to end it after a string of setbacks.”
‘I knew I’d been a fool but I couldn’t shake off the depression at feeling what a failure I’d become.”
Windass said he could not cope after finishing his career and began drinking, often consuming 15 pints of lager and lime.
He said his marriage broke up and with little income, estranged from his family and grieving for his father John who had recently died, he decided to kill himself.
Luckily a former girlfriend turned up and saved him.
He said the following day, he tried again to take his own life.
‘I tied it to a handrail at the top of the stairs but it was too long. I was quite drunk and couldn’t get it to work so I got a belt instead. At that point a friend came round so I couldn’t go through with it.”
He added: ‘We’re not the brightest but you play football all your life. There are hundreds of footballers in the same boat (after retirement). There is nothing to get up for in the morning.’