By 'old files', I assume you mean files you have already deleted. Eraser, as you have seen, fills the free space with random data, then wipes the free entries in the MFT. But if the file system has reserved some space, for example for shadow copies or the contents of System Restore points, that space will not be wiped. The issue is not your OS version, but, assuming that it is NTFS, the way the file system works together with Windows to make (and then, often, protect), copies of data all over your drive. For better privacy, turn off shadow copies on all drives, and System Restore on any non-system drive. Also, use the Windows feature to wipe the paging file on shutdown once in a while.
The best way to erase files securely is to do it directly; then Eraser will be aware of shadow copies and deal with them. Free space wiping is an extra layer of security, but is not necessarily the complete answer, particularly on a system drive. You don't say which file recovery program you are using. I use, among others, Recuva, which has a useful feature to erase any files it finds (if it can; there are files it cannot erase). This usefully complements what Eraser can do.
I find that programs like Eraser do a much better job on non-system drives, and therefore try to segregate programs and data on to physically separate drives.
Without more details, this general response is the best I can do. If you are able to describe your particular issue step by step, I may be able to help further.
One final thing. The Eraser Window may say Version 6.0.6, but please check Help|About. It may say 6.0.7, which is the current 'stable' version. If it still says 6.0.6, upgrade to 6.0.7, which has a lot of bug fixes.
David