The equivalent of 999 under todays rules governing the Roman numeral system is CMXCIX
But the Romans themselves in the past would have worked out the equivalent of 999 on an abacus counting device as DCCCCLXXXXVIIII and simply changed it to IM (1000-1) in written form
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C d m
The greatest value two digit number in Roman numerals would be [MM] with a horizontal bar placed above it, which would represent the number 2 Billion. In generally used Roman numerals MM represents 2000.
999 is IM Roman numerals = 1000-1
The Roman numeral for 10 is X
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