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I don't use Windows, but I am reasonably sure that if you are using Windows 7, you can sync your Outlook and iPad via iCloud. The trick is to make sure you choose to Merge or Keep you contacts when prompted. I don't remember what it says. Just don't choose Delete.
If you are syncing with iCloud you can also go to icloud.com in a computer browser. From there you can export your contacts as a vCard file. Outlook should have no problem importing this file. Hold in mind this is a one time transfer. It won't keep you contacts synced.
You can do much the same thing if you are syncing with Google, going to their site to export the contacts then importing them into Outlook; or syncing your Outlook with Google (keeping an eye on merge, keep, delete options along the way.
No matter what you do, you should make a backup of your contacts. The best way is to sync with a service (like one of the above) and export them. That way you have a file to recover from no matter what happens. But at the very least, back up the iPad. You would have to restore the entire iPad to get back the contacts, but at least you'd have that choice.