Under today's rules 99,999 written in Roman numerals is: (XCIX)CMXCIX
Numerals in brackets indicate multiplication by a thousand.
Hence:
(XCIX) = 99*1000 = 99,000
CMXCIX = 999
But today's rules governing the Roman numeral system were introduced during the Middle Ages so it's quite possible that the Romans themselves would have calculated the number 99,999 on a abacus counting device as (LXXXXVIIII)DCCCCLXXXXVIIII and then simply wrote it down as I(C) meaning minus 1 plus 100,000 which equals 99,999.
To write 99999 in Roman numerals, you would use the symbol for 100,000 (C) to represent the digit 9 and then subtract 1 (I) from it to represent the digit 99. Therefore, 99999 in Roman numerals would be written as C(IM).
IC (C with line over it).
42 in Roman numerals is XLII.
MMMM
MCMLXXXVII
DCCXXXII
DCXXV
LXXXIII
MM
22 in roman numbers is "XXII"
In today's terms it is written out as (XCIX)CMXCIX but the Romans themselves would have probably wrote it out simply as I(C) which means -1+100,000 = 99,999
It is: 753 = DCCLIII
It is: 2000 = MM