... multiple names I am attempting to match. ... Just added if statements in the while loop.

if-statement patches are probably ok for one-off or infrequent runs with a small, stable city-name list. For larger lists of cities or more frequent runs, I think I would go with a database.

It's also possible to use a regex/hash approach:

c:\@Work\Perl\monks>perl -wMstrict -MData::Dump -le
"my @cities = ('windsor riverside', ' new york ', 'philadelphia',);
 ;;
 my $rx_city = build_city_regex(@cities);
 print $rx_city;
 ;;
 my %city_digits;
 ;;
 RECORD:
 for my $record (
     'CA006139520,\"WINDSOR RIVERSIDE, ON CA \",2018-01-02,10',
   qq{CA006139520,\"  NEW  YORK  , ON CA \",2018-01-02,987\n},
     'CA006139520,\"NEWYORK, ON CA \",2018-01-02,9999',
     'CA006139520,\"NEW YORK, ON CA \",2018-01-02,10210',
   qq{CA006139520,\"PHILADELPHIA, ON CA \",2018-01-02,76\n},
   ) {
   next RECORD unless
     my ($city, $digits) = $record =~ m{ ($rx_city) .* \b (\d+) \Z }xm
+s;
   push @{ $city_digits{ canonicalize_city($city) } }, $digits
   }
 dd \%city_digits;
 ;;
 sub build_city_regex {
   my ($regex) =
     map  qr{ \b (?: $_) \b }xms,
     join ' | ',
     map  { (my $c = $_) =~ s{ \s+ }'\s+'xmsg;  $c; }
     reverse sort
     map  canonicalize_city($_),
     @_
     ;
   return $regex;
   }
 ;;
 sub canonicalize_city {
   my ($city_name) = @_;
   ;;
   die qq{bad city: '$city_name'}
     if $city_name =~ m{ [^[:alpha:] -] }xms;
   $city_name =~ s{ \A \s+ | \s+ \z }''xmsg;
   $city_name =~ s{       \s+       }' 'xmsg;
   $city_name = uc $city_name;
   ;;
   return $city_name;
   }
"
(?msx-i: \b (?: WINDSOR\s+RIVERSIDE | PHILADELPHIA | NEW\s+YORK) \b )
{
  "NEW YORK"          => [987, 10210],
  PHILADELPHIA        => [76],
  "WINDSOR RIVERSIDE" => [10],
}
[download]

Something like this will work even with large lists (thousands!) of city names. However, as I said, for a sufficiently high size-frequency metric, it's probably better to use a database.

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