$re = '/\d{1,}[ ][A-Z][a-z]{2}[ ](?:\d{4}[ ]\d{2}[:]\d{2}|\d{2}[:]\d{2})[\s\S]*?(?:(?!\n\n)[\s\S])*?(?=\n\d{1,}[ ])|\d{1,}[ ][A-Z][a-z]{2}[ ](?:\d{4}[ ]\d{2}[:]\d{2}|\d{2}[:]\d{2}).*/m';
$str = '...
...
15 Apr 2014 22:05 - id: content
15 Apr 2014 22:09 - id: content
15 Apr 2014 22:09 - id: content
with new line
16 Apr 2014 06:56 - id: content
with new line
with new line
16 Apr 2014 06:57 - id: content
16 Apr 2014 06:58 - id: content
...
...';
preg_match_all($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