This will be quite roundabout and source light as I don't have access to my notes but:

As both Raleigh and Drake were West Country land owners and as their famous/infamous overseas ventures were closely linked it is highly likely that they did meet (they may have even been cousins but my memory fails me on this). Drake was born in Tavistock and owned Buckland Abbey for a while. Raliegh was born in Hayes Barton, had family connections in Bideford and business interests in Cornwall . Drake helped rescue some of the 1585 military colony from the Outer Banks of North Carolina; A colony which was organised under Raleigh's inherited colonial charter. Add to this that they were both active and known at the court of Elizabeth I in the same time period and it should be a certainty.

This was never something that I considered looking into when I was researching the period so my apologies. I am sure that there will be someone with access to a single source that mentions them both in the same place at the same time.

EDIT: Clarity and formatting