Online football betting, which is illegal in Singapore, is on the rise, say Gamblers Recovery Centre. Two out of five cases it sees are related to this.
His relentless gambling drove his wife to such despair that she ended up in a psychiatric ward.
He was so addicted that he took his son out of pre-school so that he could pay off his debts.
Gerald (not his real name) has lost around $400,000 betting on football matches online for the past 13 years.
The low point came when he saw how tough life was after they had to give up their five-room flat and squeeze into a room, which was all the family could afford to rent.
So he stopped gambling. It has been nine months since he placed his last bet. Having fallen off the wagon so often before, he says he must be strong for the sake of his wife and son.
Still, the going is tough.
Every day, he looks at a mountain of legal letters and bills with regret. All of them - scars of a not-so-distant past - remind him that he is still more than a quarter of a million dollars in debt.
The irony: He's not a football fan and doesn't watch the matches that he bet on.
"I was in it for the money. When I lose, I would bet again because that was the fastest way to recoup my money," said the 30-year-old, who earns about $6,000 a month as a petrochemical technician.
Each time, he would bet between $500 and $2,000 on matches involving teams he had never heard about in the English Premier League and Uefa Champions League.
To fuel his habit, he borrowed from 15 loan sharks. When he could not repay them, they came in waves to splash paint on the corridor of his parents' flat, where he was living at the time.
Said Gerald: "They also chained up the front gates of my parents' and my neighbours' flats, and scribbled messages on the walls to get me to settle my debts.
"My parents had to defend me from angry neighbours, lying that I was a wrong target or a guarantor for someone else. I borrowed from licensed moneylenders to pay off the unlicensed ones."
He knows of Manchester United Football Club - but only because he won his first bet backing them when he was 17. Back then, he was lured into it by a classmate who was a bookie in his school.
"My family was poor. My father was a drug addict who was in and out of prison, and my mother had several failed businesses. My classmate noticed this and asked if I wanted to bet.
"I won the first few games. When my classmate gave me my winnings of a few hundred dollars, it made me feel good. It also put food on my family's table," he said.
His initial winnings also paid for his dates with his then girlfriend Sarah (not her real name), who is now his wife.
Gerald was hooked, but he soon started losing. He turned to Sarah for help.
Sarah, now 31, said: "I was in polytechnic. I lied to my dad that I needed $3,000 for a course. I felt bad, but I was blinded (by love).
"I tolerated his habits because he kept reassuring me that things would get better. But each time he had money problems, he became moody and upset."
Sarah walked out of Gerald more than eight times, all because of his gambling. But they reconciled because of love after a few months apart.