$re = '/(?<log>(?<ymdhm>\d{4}-\d{2}-\d{2} \d{2}:\d{2}).*?(?<flag>Starting)$)\n\k<ymdhm>.*?\k<flag>/m';
$str = '2019-10-31 06:53:58.416 +10:00 [1] - Not Started
2019-10-31 05:49:52.416 +10:00 [1] - Starting
2019-10-31 05:49:52.416 +10:00 [1] - Starting
2019-10-31 05:49:53.416 +10:00 [1] - Starting
2019-10-31 05:50:53.416 +10:00 [1] - Starting
2019-10-31 06:53:58.416 +10:00 [1] - Starting
2019-10-31 06:53:59.416 +10:00 [1] - Starting
2019-10-31 06:53:58.416 +10:00 [1] - Ended';
preg_match_all($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