Because 90 = XC and 9 = IX so it follows that 99 is XCIX in accordance with the rules and regulations governing todays Roman numeral system introduced during the Middle Ages which had nothing to do with the ancient Romans.
But there is evidence to suggest that the ancient Romans would have calculated the equivalent of 99 on an abacus counting device as LXXXXVIIII and then abridged it to IC in written form because the Latin word for 99 is undecentum which literally means 'one from a hundred'
If we add I to LXXXXVIIII it becomes C but in order to retain its original value we must subtract I from C therfore LXXXXVIIII = IC
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99+1056 = 1155 or MCLV in Roman numerals Today we write out 99 in Roman numerals as XCIX but the Romans themselves would have probably wrote it out simply as IC (-1+100 = 99)
The number 49 in Roman numerals is XLIX and the number 99 in Roman numerals is XCIX
Today's conventional way of writing 99 into Roman numerals is XCIX. However the Romans themselves would have probably calculated 99 on a abacus counting device as LXXXXVIIII and then wrote it out as IC (-1+100 =99)
In todays modern notation of Roman numerals they represent 99
99