Cattail,

the problem with your analysis is that if a boat is five times "as big as" (i.e. five times as long, and five times as wide, and five times as high as) another ship, then its volume is about 125 times as great. Thus, a ship 5 times larger in each dimension would require 125 times as much water to fill it up. So if it took a little boat five minutes it would take the larger one roughly 625 minutes, or ten and a half hours...

Add to this the fact that the shape of a ship's hull is different from that of a small boat, exactly because the ship is made for carrying large amounts of stuff around. (The ship needs to be mostly filled with heavy stuff and still have enough buoyancy to float, which requires a greater volume). So it would almost certainly be of greater volume than simply an expanded version of a 20' boat.

This of course adds another wrinkle to the tale. Another factor on which this sinkage might depend: how much heavy stuff was in the Turkish Robbery? If she was sailing high, she would have longer to go before foundering...

BTW, I still vote no on whether this is likely, but as Teribus says (and as I said in the very first response), yes on whether it is, strictly speaking, possible. IF the boy could swim there without being detected, AND he used not an augur but some other tool like a saw, AND he was extremely skillful or lucky, so that his holes had a much greater effect together than they would have had individually (eg. Teribus' "if you drill the holes to destroy the dowling holding the planks to the frames and ribs of the hull") AND he remained undetected and unfrozen and unshot (not to say undead) during this time, AND the crew was for some reason unable to pump out the water or patch the hole, THEN he might have a hope of sinking a ship in this manner.

I do not think this was a method of sinking ships in the Elizabethan era, though as Ebarnacle says, it may have been "a standard method of attack." Remember, the goal in fighting a ship is often not to sink it but to force its crew to surrender so that you can take the ship for yourself. By drilling holes you could divert the crew from fighting, and toward pumping and patching, giving yourself an easier job. Once you had subdued the crew, you could then repair the ship. But whether it was used to SINK ships? Of that I remain skeptical!