In accordance with the modern rules now governing the Roman numerals system it will be the year of 2088 which in Roman numerals is written as MMLXXXVIII that will have the most numerals in it but if we were to write out 2099 in the same way that the ancient Romans once did then that would be even longer but instead we would now consider 2099 to be MMXCIX instead of its real original notation which once was MMLXXXXVIIII and could have been abridged to IMMC.
QED
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It will be as the ancient Romans would have notated it MMLXXXXVIIII = 2099
Presumably you mean what date will have the most Roman numerals in the 21st century? If so then it will be December 31 2088 which will be: XII-XXXI-MMLXXXVIII actually, August 28, 2088 will be the most Roman Numerals in the 21st Century: VIII-XXVIII-MMLXXXVIII
The year so far which has required the most Roman numerals to represent would probably be 1888, which is MDCCCLXXXVIII
Of the years that have already occured probably the longest in Roman numerals is 1888, which is MDCCCLXXXVIII
Of the years that have already occured probably the longest in Roman numerals is 1888, which is MDCCCLXXXVIII