re = /\b(Cl(?:vland|and|ev))\b/m
str = 'City of Cleveland
City of Clvland
City of Boston
City New York
City of Clev
City of Miami
City of Cland
Cle Ci'
subst = 'Cleveland'
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