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MCMXCIX

MIM (Should work as well, and easier to write)

Improved Answer:-

In accordance with the rules governing the Roman numeral system made during the Middle Ages and centuries after the Romans had left England 1999 in Roman numerals is considered to be MCMXCIX.

But there is strong evidence to support the fact that the Romans themselves would have probably calculated 1999 on an abacus counting device as MDCCCCLXXXXVIIII and by placing I to both sides of these numerals would have simplified them to IMM (-1+2000 = 1999) in written form.

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14y ago

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