my @candidates = qw( http://www.someplace.com/foo http://www.someplace.com/foo/bar http://www.someplace.else.com/foo ); my $target = 'http://www.someplace.com/foo/fighter/index.html'; my %leader = ( uri => '', length => 0 ); foreach my $candidate (@candidates) { if( $target =~ /^$candidate/ ) { if( length($candidate) > $leader{length} ) { @leader{'uri','length'} = ($candidate,length($candidate)); } } } if( $leader{uri} ) { print $leader{uri},',',substr($target,$leader{length}); } else { print "no matches" }