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Because we are still taught the Roman numeral system under rules introduced during the Middle Ages which converts 99 into Roman numerals as XCIX (90+9 = 99) but these rules were made in a haphazard manner centuries after the fall of the Roman Empire.

In all probability the Romans themselves would have calculated 99 as LXXXXVIIII and by placing I to both sides of these numerals simplified them to IC (-1+100 = 99)

In fact the Latin word for 99 is "undecentum" which literally means one from a hundred.

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13y ago
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Q: How can 99 be IC in Roman numerals when you are taught that it is XCIX?
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