There was a setting to turn of SFN's in Windows 95, (Or maybe only NT4 on FAT) so it's not totally impossible.
NT & Co.:
Under HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Control\FileSystem
REG_DWORDs: NtfsDisable8dot3NameCreation Win31FileSystem Win95TruncatedExtensions
Cheers,
Oliver