How do you match only valid roman numerals with a regular expression?

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You can use the following regex for this:

^M{0,4}(CM|CD|D?C{0,3})(XC|XL|L?X{0,3})(IX|IV|V?I{0,3})$

Breaking it down, M{0,4} specifies the thousands section and basically restrains it to between 0 and 4000. It’s a relatively simple:

   0: <empty>  matched by M{0}
1000: M        matched by M{1}
2000: MM       matched by M{2}
3000: MMM      matched by M{3}
4000: MMMM     matched by M{4}

You could, of course, use something like M* to allow any number (including zero) of thousands, if you want to allow bigger numbers.

Next is (CM|CD|D?C{0,3}), slightly more complex, this is for the hundreds section and covers all the possibilities:

  0: <empty>  matched by D?C{0} (with D not there)
100: C        matched by D?C{1} (with D not there)
200: CC       matched by D?C{2} (with D not there)
300: CCC      matched by D?C{3} (with D not there)
400: CD       matched by CD
500: D        matched by D?C{0} (with D there)
600: DC       matched by D?C{1} (with D there)
700: DCC      matched by D?C{2} (with D there)
800: DCCC     matched by D?C{3} (with D there)
900: CM       matched by CM

Thirdly, (XC|XL|L?X{0,3}) follows the same rules as previous section but for the tens place:

 0: <empty>  matched by L?X{0} (with L not there)
10: X        matched by L?X{1} (with L not there)
20: XX       matched by L?X{2} (with L not there)
30: XXX      matched by L?X{3} (with L not there)
40: XL       matched by XL
50: L        matched by L?X{0} (with L there)
60: LX       matched by L?X{1} (with L there)
70: LXX      matched by L?X{2} (with L there)
80: LXXX     matched by L?X{3} (with L there)
90: XC       matched by XC

And, finally, (IX|IV|V?I{0,3}) is the units section, handling 0 through 9 and also similar to the previous two sections (Roman numerals, despite their seeming weirdness, follow some logical rules once you figure out what they are):

0: <empty>  matched by V?I{0} (with V not there)
1: I        matched by V?I{1} (with V not there)
2: II       matched by V?I{2} (with V not there)
3: III      matched by V?I{3} (with V not there)
4: IV       matched by IV
5: V        matched by V?I{0} (with V there)
6: VI       matched by V?I{1} (with V there)
7: VII      matched by V?I{2} (with V there)
8: VIII     matched by V?I{3} (with V there)
9: IX       matched by IX

Just keep in mind that that regex will also match an empty string. If you don’t want this (and your regex engine is modern enough), you can use positive look-behind and look-ahead:

(?<=^)M{0,4}(CM|CD|D?C{0,3})(XC|XL|L?X{0,3})(IX|IV|V?I{0,3})(?=$)

(the other alternative being to just check that the length is not zero beforehand).

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