Prior to that I'd say a great deal. In the last 10 years though? Not in my mind.
The advent of cheap femto clocks and DACs which do much better with Redbook (44.1kHz/16 bit stereo) than the previous generation happened around 2000 or so.
After that I think it's all taste making rather than actual improvements in tech.
Prove me wrong by sending me the latest dCS stack to listen to for a couple of years.