$re = '/-\s*(?<what>.*):.*?(?<device>ip(?:hone|ad(?: ?air)?))\s*(?<model>\d)?.*ios\s*(?<os>\d)/mi';
$str = '1. Automated - Under the Hood: iPhone 6 running iOS 9
2. Automated - AU/NZ: iPhone 6 running iOS 9
3. Automated - DRM: iPhone 6 running iOS 9
4. Automated - Ads regression: iPhone6 running iOS 9
5. Automated - Ads regression: iPhone 5 running iOS 8
6. Automated - UI & Functional Regression: on iPad 2 running iOS 8
7. Automated - Under the Hood: iPad Air on iOS 8
8. Automated - AU/NZ: iPad Air running iOS 8
9. Automated - DRM: iPadAir running iOS 8';
preg_match_all($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