2 Drivers Sharing Same Sealed Enclosure at Different Crossover Frequencies

This is one of those topics for which the answer is "it depends" if you really answer the OP's question, as it has been posed. For example, on the web page from Zaph the two woofers use a first order shelving filter. This will result in a low phase difference between the two drivers, maybe 45 degrees at most, and with one being rolled off it works fine. If that is all you plan to do there is no need to read further.

If on the other hand you chose to use a higher order filter (above second order), the additional phase shift might cause some undesirable effects because the phase rotation will be beyond 90 degrees before there is significant rolloff. So in general this might not work well in some cases. Choose wisely. It should not be too difficult to model this in a crossover simulator so you can test out scenarios for your particular project.
 
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