re = /(?=\b[MCDXLVI]{1,6}\b)M{0,4}(?:CM|CD|D?C{0,3})(?:XC|XL|L?X{0,3})(?:IX|IV|V?I{0,3})/mi
str = 'Act IX: The End
Act iX: The End
Act Ix: The End
Act ix: The End
Act IX : The End
Act iX : The End
Act Ix : The End
Act ix : The End
i also me
only ii two
the iii three
what about iv
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
'
subst = '\\U$0'
result = str.gsub(re, subst)
# Print the result of the substitution
puts result
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 Ruby, please visit: http://ruby-doc.org/core-2.2.0/Regexp.html