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Presumably you mean what date will have the most Roman numerals in the 21st century?

If so then it will be December 31 2088 which will be:

XII-XXXI-MMLXXXVIII

actually, August 28, 2088 will be the most Roman Numerals in the 21st Century:

VIII-XXVIII-MMLXXXVIII

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10y ago

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