In today's notation of Roman numerals it is CCXCIX but the Romans themselves probably wrote it out simply as ICCC (300-1 = 299)
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CCXCIX
In today's notation of Roman numerals they represent 299 in Hindu-Arabic numerals
It can mean 299 in Roman numerals because ICCC = 300-1 = 299
299 is probably the intended meaning of this improperly formed Roman numeral .
You write 1533 in roman numerals like this: MDXXXIII