$re = '/^(I[VX]|VI{0,3}|I{1,3})|((X[LC]|LX{0,3}|X{1,3})(I[VX]|V?I{0,3}))|((C[DM]|DC{0,3}|C{1,3})(X[LC]|L?X{0,3})(I[VX]|V?I{0,3}))|(M+(C[DM]|D?C{0,3})(X[LC]|L?X{0,3})(I[VX]|V?I{0,3}))$/m';
$str = 'I
II
III
IV
V
VI
VII
VIII
IX
X
XI
XII
XIII
XIV
XV
XVI
XVII
XVIII
XIX
XX
XLIV
XLIX
LXXIX
XCIV
XCIX
C
CI
CII
CIII
CIV
CVI
CIX
CD
CM
CC
CCC
D
DC
DCC
DCCC
CX
CXX
CXIX
CMXCIX
MCMXLIV
MMMMCCCXII
';
preg_match_all($re, $str, $matches, PREG_SET_ORDER, 0);
// Print the entire match result
var_dump($matches);
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for PHP, please visit: http://php.net/manual/en/ref.pcre.php