Hi, if the format used for the date in each line is the same, I suggest you parse the dates and sort by comparing them either as epoch values or with a built comparator, eg using DateTime or the core module Time::Piece.

Update: Here's a slightly silly example. (It's silly because you shouldn't be using a string sort for this, but rather, offloading the log entries into a database (eg using DBD::SQLite) and doing your sorting there.)

Parsing the dates each time the sort sub made a comparison would be grossly inefficient so I replace them with epoch values and then revert after the sort. This is not to say that sorting with a sub that uses regular expressions is not also hugely inefficient ;-)

use strict; use warnings; use feature 'say';
use Time::Piece;
use Data::Dumper;

my $fmt = '%a %b %d %T %Y';

say for map {
    s/
      (?<=TIMESTAMP=) (\d+)
    /
      localtime($1)->strftime($fmt)
    /arex
} sort {
    ($a =~ /(?<=TIMESTAMP=) (\d+)/ax)[0] <=> ($b =~ /(?<=TIMESTAMP=) (
+\d+)/ax)[0]
} map {
    chomp;
    s/
      (?<=TIMESTAMP=) (\w+\s+\w+\s+\d+\s+\d+:\d+:\d+\s+\d+)
    /
      Time::Piece->strptime($1, $fmt)->epoch
    /arex
} <DATA>;

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

Output:

$ perl 1225106.pl
...bla TIMESTAMP=Fri Oct 05 00:08:28 2018 bla...
...bla TIMESTAMP=Tue Oct 16 13:10:00 2018 bla...
...bla TIMESTAMP=Fri Nov 02 10:11:03 2018 bla...
...bla TIMESTAMP=Fri Nov 02 10:11:28 2018 bla...
[download]

Hope this helps!