re = /[\n\r].*(\d\.\s+)(?!.*[\n\r](\d\.\s+)).*((<br\s*\/?>){2})/m
str = '<br><br><br>. Do not replace <br> here.
1. One
2. Two
3. Three<br><br><br>End of List. Replace first two <br> with \\n
New line follows.
<br><br><br>. Do not replace <br> here.'
# Print the match result
str.scan(re) do |match|
puts match.to_s
end
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