In theory it should, thumb drives are detected by windows as removable media in much the same ways as the drives in a raid array. You would have to use a software array manager though as i'm pretty sure there isn't a bios around that supports USB Raid. Wether windows would allow you to boot from the array is doubtful, until windows boots and loads the raid software i *think* it would be seen as a 2 seperate drives. Were you thinking of running a raid-0 or raid-1 array?
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