On Ubuntu 20.04 the problem is still happening pretty similar to the one
reported by the OP. I've found a new way to fix it though.

Steps to reproduce:
1. turn off machine.
2. leave a headphone plugged in
3. turn on machine (caveat: if your laptop is suspended from here the bug won't 
be produced)
4. unplug headphone
5. plug headphone -> YOU WON'T HEAR A THING

To fix it I do:
I open Settings -> Sound and there:
1. change the Input Device to internal microphone (not the headphone) (you 
should start hearing after this step!!!)
2. Change the Input Device to the headphone

(this fix is faster than suspending and bringing it back up).

Another fix, is to always unplug the headphones when turning off the
laptop.

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https://bugs.launchpad.net/bugs/1575078

Title:
  [XPS 15 9550, Realtek ALC3266] Headphone jack stops working after a
  while

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