$re = '/(\S+)(?=\s+\b(\d{2}([-/ .])\d{2}\3\d{4})\b(?!.*\b\d{2}([-/ .])\d{2}\4\d{4}\b))/m';
$str = 'Florida 03/22/2022 04/05/2022 Bid Support Help Desk is glad to assist you
Florida 04/05/2022 Bid Support Help Desk is glad to assist you';
preg_match_all($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