re = /Debuted (.*) and peaked at (.*) on the (.*)\. Source: (.*)\. Label\/Number: (.*)\. Date Peaked: (.*)\./m
str = 'Debuted 11/03/1958 and peaked at #38 on the Hot 100 Chart. Source: Pop Annual. Label/Number: Ace 551. Date Peaked: 12/01/1958.
Debuted 11/30/1957 and peaked at #1 on the Hot 100 Chart. Source: Pop Annual. Label/Number: ABC-Paramount 9871. Date Peaked: 12/28/1957.
Debuted 09/15/1958 and peaked at #1 on the Hot 100 Chart. Source: Pop Annual. Label/Number: MGM 12677. Date Peaked: 11/10/1958.'
subst = '$1==$2==$3==$4==$5==$6'
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