...short answer, is 'probably not' ... longer version goes like this...
... mentioning the actual device model and/or USB pid/vid would've helped me
here, but, the position can be deduced from your post, and that'll tell you
if you end up at the short answer =) ....
... if the device itself needs drivers ...ie; there's no native driver
support in the linux kernel drivers ... you're sunk. Simple case of 'if
there is no way for the linux kernel to address the device, then any other
software running on that kernel will not be able to address the device either'...
... if the device does not need drivers ... that is, if there are native linux
kernel driver supports and/or proprietary drivers that enable the kernel to
address the device, then software (like crossover/wine) should be able to 'see'
the device, and communicate with it via the linux kernel. However, then the
problem arises regarding -how- such kernel communications take place, and for
these devices, in Windows, a -lot- of the time that involves 'activex' which
is not so complete in wine ; in fact, some of activex necessitates a 'real'
Windows kernel be running to work at all, and win32 apps reliant on such, will
obviously fail to work...
... I should also mention, if the linux kernel does support the device, it's
very likely the device nodes will appear differently than how they appear on
a Windows system, but like I say, even when it's possible to work around that,
invariably other things fail due to the lack of a 'real' Windows kernel being
available ... but like I say, in this chain, the very first thing that needs
to happen (practically speaking), is the linux kernel driver link to the device.
Without that, you can go no further....