Having just picked up SH4 about a week ago, I haven't encountered too many DD's yet, so I don't have one that scares me.
What does scare me, however, are H6Ks, flying boats have become the bane of my existence. I've only died to two of them, second one caught me completely off-guard in a storm and wasn't spotted until he was about 2nm's away (I was in an S-boat, so there was no avoiding that beating).
First one is the most ridiculous death I have ever experienced playing any SH title. My first career, first patrol, heading out of Manila in command of the S-38. I was maybe 10nm out of the harbor when my watch crew calls out that they've spotted an aircraft. I'm in friendly waters, so I assumed it was friendly (I did not know at this time that the game only does the popup for hostile contacts) and went on my merry way. I was terribly surprised when a few hundred kilos worth of explosives smashed my little boat to pieces. I guess that's what I get for clicking the 'Campaign' button before reading..well, anything actually.
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The only sound that still scares me to this day...
The silence when the pinging stops. 
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