If i clone a hard drive using the 'dd' command, will it also clone the free space and information about deleted files?

Solution 1:

Yes, dd clones every bit on the drive, including deleted files and free space.

You could also look into CloneZilla, which is a user-friendly LiveCD for cloning and restoring disks, though I'm not sure its disk-image format would be compatible with your Windows software. http://clonezilla.org/