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Are my winnings from overseas casinos taxable in Singapore?

In Singapore, your tax liability is only for income received in Singapore. This means that you pay tax on income you receive locally. There is no capital gains tax in Singapore. Casino winnings either locally or overseas are considered capital gains and not subject to taxation.

In other words, you do not need to declare the winnings. And even if you do, it is unlikely that you will have to pay tax on them.
If you do not declare the winnings, do ensure that you are keeping records of having won – just in case you are called to explain the sudden girth in your bank account.

The concern in Singapore is that we do not become a facilitator in the illegal laundering of money. While there is relatively free movement of cash in and out of Singapore, the qualification on this is that so long as the monies can be traced back to a legitimate source, there will be no problems.

Finally, it is interesting that you think you will actually have substantial winnings from a casino to worry about paying tax on. Don’t you know that the house always wins? If you visit a casino, you may come out not being able to even afford the GST on a candy bar!