$re = '/\d+\/\d+\/\d+\s*?\d+:\d+:\d+\s*?[AP]M/m';
$str = '12345 User Name 9/10/2018 11:39:37 AM Valid Entry Place1
12345 User Name 9/10/2018 12:48:43 PM Valid Exit Outside Place1
12345 User Name 9/10/2018 1:00:44 PM Valid Entry Place1
12345 User Name 9/10/2018 2:17:01 PM Valid Exit Outside Place1
12345 User Name 9/10/2018 3:23:36 PM Valid Entry Place1
12345 User Name 9/10/2018 3:25:56 PM Valid Entry Place1
12345 User Name 9/10/2018 6:06:25 PM Valid Exit Outside Place1
12345 User Name 9/10/2018 6:07:55 PM Valid Entry LC
12345 User Name 9/10/2018 6:28:19 PM Valid Exit Outside LC
12345 User Name 9/10/2018 6:30:06 PM Valid Entry Place1';
preg_match_all($re, $str, $matches, PREG_SET_ORDER, 0);
// Print the entire match result
var_dump($matches);
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