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Money Confessions: I Won $572,571 From TOTO, And This Is What I Did With My Money

Kendra Tan

Kendra Tan

Last updated 20 February, 2023

Patience paid off — to the tune of more than half a million — for a 58-year-old Singaporean man who regularly bets on TOTO.

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The day was 16 December 2017. I was on my way to work when I decided to stop by an NTUC outlet at Dawson Place to place my regular S$1 TOTO bet for the draw on 18 December 2017

As I often bet (two times a week, for each draw), my habit was to check all my tickets at one go, once every two months. 

Fast forward to February 2018, I decided to dig all my bets out and check them online. Now, I don’t exactly remember which day it was, but it was close to 11pm when I had just two or three slips left. 

‘Are my dreams of hitting the jackpot coming true?’ I thought to myself as I scanned the website for the sixth and final number. Lo and behold, it was a perfect match — I had officially won the top prize of S$572,571.

I was very lucky to have checked my ticket on time, because prizes must be claimed within 180 days (including weekends and public holidays) from the date of the draw. I collected my prize just a few weeks shy of Chinese New Year, one month before the deadline.


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Bought numbers with special and personal meaning

The key is consistency. I usually buy numbers that are important to me, like my car plate number, address and birthday.

The winning number was a broken-down combination of my birth date into day, month, year and age.


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First time winning such a huge amount of money 

Over the years, I’ve won small amounts but never this big of a windfall. I couldn’t believe it. I quickly woke my wife up and asked her to double-check my slip in case my tired eyes were playing tricks on me. The next morning, I frantically called the outlet to confirm my winnings. 

Reality only sunk in the day after when I was on my morning jog and realised that I had achieved my dream of winning big at TOTO. I suddenly had an extra bounce in my steps and life seemed like a fairytale. 

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Collecting my winnings at the Singapore Pools HQ

Together with my wife, we had a simple breakfast of kopi and kaya toast before walking over to the Singapore Pools HQ. 

We waited calmly for my queue number to be called before going to the counter and producing my IC and winning slip. The clerk handed me a cheque with my name on it. The entire situation felt like a dream. Through it all, I was particularly happy that all my financial worries such as paying for my daughter’s education were settled. 

When we left, I kept telling myself to act normal. As I can be quite reckless with money, I handed the entire cheque to my wife and returned to work after that. 

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The first thing I did with half a million dollars

The first thing I did after getting the cash was to give S$10,000 to a few of my closest family members as a small token of appreciation. I was firm in not letting the rest of my relatives and friends know as I did not want any attention or requests from them. 

I also wanted to return the good fortune in a small way. I decided to pledge S$5,000 to help local charities. Besides donating to underprivileged children, I gave part of my winnings away in the form of ang paos and lunches to a nursing home too. 

💡 Did you know? You can file for personal income tax relief for your charity donations.

Invested the rest

As an ex-banker, I was concerned with inflation eating away at my money. It also didn’t help that bank interest rates were so low when I won the lottery. 

With that, I put the rest of my winnings into two types of investments. 

I bought a retirement insurance plan worth about S$150,000, with a projected return amount of S$350,000, 20 years from now.

Next, I purchased S$50,000 worth of Singapore bonds and DBS shares.

On the side, I made a S$350,000 downpayment for a condominium. While this was not specifically for investment purposes, the property purchase was to ensure the remainder of my winnings are parked in an asset to control my spending.



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Here’s a breakdown of how I used S$572,571:

  • Retirement insurance: S$150,000
  • Condo downpayment: S$350,000
  • Singapore bonds: S$50,000
  • Family: S$15,000
  • Charity donation: S$5,000

For all past, present and future lottery winners, here is my advice — it is easy to be sucked in and overindulge in an unnecessary lifestyle, especially after winning big.

Instead of buying a luxury car or branded goods, invest and plan for this money to grow so that it can help you retire comfortably (if you win young, that is). Don’t let inflation eat into your winnings. 

See also: Best Savings Accounts in Singapore to Stash Your Cash (2023)


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As told to Kendra Tan

Even lottery winners need a financial plan. Having the discipline to manage your winnings is part of that plan. You can also further that windfall into a solid wealth accumulation option. Besides putting your winnings into some form of savings, such as an endowment plan, consider putting a small amount into robo-advisors to grow your wealth, whether you win the lottery or not. 

If you're lucky enough to land such a windfall, that will also give you the opportunity to open a priority banking relationship with a bank. A priority banking account typically requires deposits upwards of S$200,000 and will give you access to the services of a relationship manager, exclusive lifestyle privileges and more.


Read these next: 
I’m 27 And I Accumulated My First S$100,000 By Investing And Saving Over 4 Years
Money Confessions: 9 Singaporeans Share Their Portfolio Asset Allocation
These 11 Horror Stories Will Get You ‘Woke’ About Your Personal Finance
I’m An Actor And I Went Broke. This Is How I Bounced Back: Nat Ho
I’m A Freelancer And I Save $800 A Month

Avid promo code hunter and haggler. Kendra doesn’t like paying full price for anything. She’s the best person to bring along if you’re travelling on a budget. Have an interesting story to tell? E-mail her at


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