Yes and no. Depends what software and hardware combination(s) is being used. There are software players that can correct for most if not all defficiences in say a lowly redbook. But it takes one hell of a computer and understanding/experience on the part of the user. But better is lower resolution done right than something potentially better but not executed well enough. This is where $ inevitably will kick in - a really well done redbook will outperform a poorly made "higher rez", whatever that might be, PCM or DSD.
This is why I decided not to go with Foobar2000 ABX plugin comparator - it can only ABX in PCM, meaning you can not compare native DSD vs PCM under ABX .
Even "sighted" AB will at least give away there was change from PCM to DSD - there is slight switching noise, again dependant on software adjustment and actual hardware. And that actual hardwares can sound sufficiently different one from another to mask the (dis)advantages of either PCM or DSD - often preffering one and shunning the other. And/or vice versa.
But given the same kind of attention to detail ( with inevitable price increase ), upconverted 24/192 should have the edge. IF the soft is clever enough to "recostruct" what should have been there in the redbook but can not be due to the very redboook itself.
Not a straight answer, but one I believe is close to the truth.