I think the problem is everything between the lines
### BEGIN AUTOMAGIC KERNELS LIST
and
### END DEBIAN AUTOMAGIC KERNELS LIST
gets auto regenerated when a new kernel is installed, and update-grub is
run.
see bug 21412 and bug 2646.
What happens if you copy the windows entry above ### BEGIN AUTOMAGIC
KERNELS LIST and run sudo update-grub ?
** Changed in: grub (Ubuntu)
Status: Unconfirmed => Needs Info
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Updating Kernel modified Grub doesn't respect customised entries
https://launchpad.net/bugs/59895
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