$re = '/^(This is some header \d+)[\s\S]+?^(Repeated item \d+)\s*^(Repeated item.*)[\s\S]+?(Repeated item \d+)\s*^(Repeated item.*)/m';
$str = 'This is some header 1
nonsense text 1
Repeated item 1
Repeated item 1 Data
nonsense text 1
Repeated item 2
Repeated item 2 Data
This is some header 2
nonsense text 1
Repeated item 1
Repeated item 1 Data
nonsense text 1
Repeated item 2
Repeated item 2 Data';
preg_match_all($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