Is the watch recognised by Ubuntu itself?
Sadly Wine doesn't support USB drivers at this stage so this is probably the 
problem.
Could you try running the program from the terminal as per 
http://wiki.winehq.org/FAQ#get_log and attaching the log here

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https://bugs.launchpad.net/bugs/734467

Title:
  Trying to run My Timex Datalink with Xubuntu

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