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999 is IM Roman numerals = 1000-1
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Yes under today's rules governing the Roman numeral system XCIX is 99 But during the Roman era the equivalent of 99 was probably IC (100-1 = 99)
ICIX is not used; if it were that is 99 (IC) +9 (IX) = 108 which is not a 2 digit number 99 is the maximum two digit number; in Roman Numerals, that is XCIX
The number 10 has a roman numeral of X. The number 50 has a roman numeral of L. These are the only 2 digit numbers with a single value.