Mac Passport Missing Files

Recently some files went missing from my computer, they were stored in a file on our PC server (I also use Parallels) but the folder was on the MAC side as well.  The entire folder is gone and unfortunately I emptied my trash (honestly I do not even know if it was deleted and in there), I have tried unhiding folders, that didn’t find it, I installed a program to recover deleted files and that didn’t find it.  Then I went into my Passport and went back to a date that I still had the file, well it is gone from there too.  Isn’t it supposed to appear as it did on that backup day???  I really need these files back and if someone knows what happened or can suggest something to try please let me know.

To recover my data, recuva or testdisk, have work for me before.