If your dates are showing in the format mm/dd/yy, than these are strings. The best thing to do is convert to the proper datatype by creating a new field and copying the data across, then deleting a column and renaming the created on. You can use the mysql conversion functions for that.
The same function can be used to convert it on the fly:
ORDER BY STR_TO_DATE(date, '%m/%d/%y'), which of course will be slow slow.
To upgrade apache and 5.4 PHP, make sure you grab the httpd from the Apache lounge, not apache.org. You'll also need the appropriate handler (php5apache2_4.dll) which I believe is a separate download at the lounge.