This one got me _so_ many times - `drupal_match_path()` is expecting a newline character to separate the paths. Add this function to your project and never look back:

    function _get_path_pattern_string(array $items) {
      return implode("\n", $items);
    }

Example usage (overly verbose):

    $patterns = array('portfolio/*', 'photo-blog', 'something-else');
    $pattern_string = _get_path_pattern_string($patterns);
    if (drupal_match_path($path, $pattern_string)) {
      // Do something...
    }

Be sure to use double quotes to surround the `\n` character.