Since MC uses the filename (including the path) as the primary file identifier and the playlists inside the library consist of these files what you ask is difficult to achieve if the filename paths are completely different.
Normally, I would recommend the following re-rip procedure:
1. Organize an off-line copy of the old library (all files disconnected) using the
[Album Artist (auto)]\[Album]\[Disc #]\[track #] filename structure
so that the actual filenames will be e.g. 01.wma, 02.wma, 03.wma etc. (i.e store the track names only in the library)
2. Rip the lossless files to a new separate library using same filename & folder structure. No CD database lookup is needed. Just take care that the Artist and Album tags are correct. You can delete this library after the re-rip process is finished.
3. Load the off-line library. Use the Find and Replace tool for fixing the filename extensions (and the base path if needed) so that they match with the re-ripped files.
4. After the new files are correctly linked with the library use the
a) Update Tags (from library) and Update Library (from tags) tools (in this order) for updating file data
b) Rename Files From Properties tool for changing the [Album Artist (auto)]\[Album]\[Disc #]\ paths and [track #] filenames to what you prefer to use.
c) Analyze Audio tool for re-analyzing the replay gain values if you use Volume Leveling (a lossless format may have slightly different peak values).
EDIT
I forgot to mention that the Auto-Importer should be disabled during this kind of operations.