I believe OrangeCD itself manages the 'Last Time Played' field. I just tested a recording I haven't listened to for awhile, and when I clicked my play link it launched Winamp. The Last Played date updated immediately, but I did have to hit the refresh view button in OrangeCD to see it. (If you're not familiar with this button, it's the one where two curved white arrows nearly touch head to tail on a green circle, in the top toolbar.)

My custom theme only displays this field on the album page. It cannot be seen on the album property sheet dialog (tabbed collection of property pages). I haven't worked on themes in awhile; I don't remember if that field exists on a per track basis or not. It's also not in the track property sheet dialog.

I see no reason why you couldn't use Windows Media player, or any other player that offers a command line interface. Having never done it, I don't know what the command lines would be. To enter the commands, select View and the Preferences to open the preferences property sheet, then click the Media tab to open the Media property page. You'll need to use the arrows to the right of the tabs to scroll the tabs until you find the Media tab.