re = /([a-zA-Z0-9,()\s.#:\/-]*?)Date From: [0-9]{2}\/[0-9]{2}\/[0-9]{4}([, \s]*[0-9]{2}\/[0-9]{2}\/[0-9]{4})*\s(Division Type: [A-Z ]*)*/m
str = 'BBB 2324 WRETY RTJE, II 1111 (000) 000-0000 Date From: 01/01/2011, 01/11/2011 AAAAA / AAAA 111 AAAA AA AAAAAA, AA 11111-1111 (111) 111-1111 Date From: 01/11/2012 '
# Print the match result
str.match(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