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That is really strange, because the file paths (in this case the dll) and the respective sizes are stored in the udd.
Normally Olly appends "_x" where x is a number to a new file with different path.
Example with MyDll.dll from 2 different paths, you should find in the UDD-Directory MyDll.udd and MyDll_1.udd.
Here is a suggestion:
Check the option "Backup old .udd files" under the Menu Options->Appearance->Directories
Restart Olly and run two sections with each of the dlls. After that there should be at least one MyDll.udd and another MyDll.bak in your current situation.
Open these two files in a HexEditor and check from Offset 62 (decimal) for their paths and size.
Regards
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