re = /<span class='indent'>.*?(<br>).*?<\/span>/
str = '<span class=\'together\'>line one,<br><span class=\'indent\'>line two.</span><br>Line three,<br><span class=\'indent\'>line four,<br>line five,<br>line six,<br>line seven;<br>line eight.<br>Line nine;<br>line ten,<br>line eleven,<br>line twelve.</span><br>Line thriteen,<br><span class=\'indent\'>line fourteen,<br>line fifteen,<br>line sixteen,<br>line seventeen,<br>line eighteen.</span></span>'
subst = ''
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