re = /.*Date Ordered:\s*(\d{1,2}\/\d{1,2}\/\d{4}).*|.*/m
str = 'Blah Blah Date Ordered: 5/19/2000 test is positive. Date Ordered: 4/2/2005 Additional testing negative.
Meh Date Ordered: 4/15/1999
irrelevant
--------------Date Ordered: 4/12/3456'
subst = '\\1'
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