I think that your best bet would be:

1. Use a data adapter to populate a DataTable with all the records.
2. Get a list of all the file names.
3. Loop through the list of file names.
4. For each file name, find the matching row, if there is one.
5. Add the image data to the row.
6. When the loop is done, use the data adapter to save the whole DataTable back to the database.

If you follow the CodeBank link in my signature, you'll find a thread on Saving Images In Databases that will show you how to get the Image data into and out of the database.