You can use Time::Piece or DateTime::Format::Strptime to parse the dates into an object (the advantage of DateTime being that it has better time zone support). If the files are small enough to fit into memory, you can use sort and a Schwartzian transform to sort them.

use warnings;
use strict;
use Time::Piece;

use List::Util qw/shuffle/;
my @input = shuffle(
    "Wed Oct  5 04:08:28 2018", "Fri Nov  2 14:11:28 2018",
    "Tue Oct 16 17:10:00 2018", "Fri Nov  2 14:11:03 2018", );

my @output = map { $_->[0] } sort { $a->[1] <=> $b->[1] }
    map { [$_, Time::Piece->strptime($_, '%a %b %d %H:%M:%S %Y')
        ->epoch ] } @input;

print "$_\n" for @output;

__END__

Wed Oct  5 04:08:28 2018
Tue Oct 16 17:10:00 2018
Fri Nov  2 14:11:03 2018
Fri Nov  2 14:11:28 2018
[download]