#!/usr/bin/env perl -l use strict; use warnings; my (%data, %seen, @order); while () { s/\s*#.*$//; next if /^\s*$/; my ($key, @rest) = split; push @order, $key unless $seen{$key}++; push @{$data{$key}}, grep { ! $seen{$_}++ } @rest; } print join ' ', $_, @{$data{$_}} for @order; __DATA__ 127.0.0.1 c2.gostats.com #SpySweeper.Spy.Cookie 127.0.0.1 ads.goyk.com # 1-800-hostingAS3321069.41.160.0 - 69.41.191.255 127.0.0.1 2a02:598:2::1095 127.0.0.2 2a02:598:2::1096 127.0.0.2 2a02:598:2::1096 127.0.0.2 2a02:598:2::1096 127.0.0.2