I would experiment with each of the calendars shown in your settings to confirm that none of them restore your ability to sync from phone to Outlook, as your symptoms are indicative of a case where the wrong default calendar is selected. Also, be sure you are viewing the correct calendar in Outlook when you evaluate whether or not it's working. Example: if you select Calendar under iCloud as your default calendar on your phone, make sure you are viewing Calendar under iCloud in Outlook when you look for the added event.
If, after experimenting in this way, you determine that none of the default calendar options restore your ability to sync your phone calendar to Outlook, the you may need to uninstall iTunes and all of its components as by following this guide: Windows XP or Windows Vista/7, then reinstall iTunes. (This will replace the Outlook plugin if that's the source of the syncing problem.) You must follow this guide exactly or it will not be successful. Note: uninstalling iTunes will only remove the application; it will not touch your iTunes library or data.
Finally, I guess I didn't ask but syncing Outlook with iCloud requires Outlook 2007 or 2010. If you are trying to use Outlook 2003, this isn't supported for iCloud syncing.