Windows only boots from one active partition (boot flag) on one drive. So all the boot files are really on the one active partition on the drive that BIOS boots from. Best to install separately, but you may be able to repair installs.
Post the link to the BootInfo report that this creates.
Boot Repair -Also handles LVM, GPT, separate /boot and UEFI dual boot.:
https://help.ubuntu.com/community/Boot-Repair
You can repair many boot issues with this or 'Create BootInfo' report (Other Options) & post the link it creates, so we can see your exact configuration and diagnose advanced problems.Install in Ubuntu liveCD or USB or:
Full RepairCD with Boot-Repair (for newer computers)
https://help.ubuntu.com/community/UbuntuSecureRemix
Older so not sure of any changes with Windows 8, but should be similar to Windows 7 and Vista.
To get each MS to have its own boot loader make a second primary NTFS partition and set its boot flag on, then install the 2nd product in it. Multibooters, Pictures here worth 1000+ words
http://www.multibooters.co.uk/multiboot.html
A user who installed two windows & it worked to boot from grub directly
http://ubuntuforums.org/showthread.php?t=1271600
Another user who disconnected and used a second drive
http://ubuntuforums.org/showthread.php?t=1334346
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