$re = '/(?=^\d{1,2}\/\d{1,2}\/\d{4})/m';
$str = '18/07/2018, 18:04 - Person2: message
18/07/2018, 18:04 - Person1: Yes
18/07/2018, 18:04 - Person2: That\'s good then
18/07/2018, 18:05 - Person1: message line 1
message line 2
18/07/2018, 18:05 - Person2: text
18/07/2018, 18:05 - Person2: But nvm
18/07/2018, 18:06 - Person1: text';
$subst = "-------------\n";
$result = preg_replace($re, $subst, $str);
echo "The result of the substitution is ".$result;
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for PHP, please visit: http://php.net/manual/en/ref.pcre.php