If the volume control of both is linear, example 1 is louder than the 2nd so of course it would sound different. However, I assume that your question is whether it is better to control the volume via Windows or via the DAC, in which case the answer is - it depends.
Digital volume control in Windows works by effectively reducing bit depth. Suppose you have a 16 bit audio file, each sample at 44,100Hz has a possible value between 0 - 65536 (2^16). Windows accomplished volume attenuation by multiplying each sample by a number less than 1, so if you want to reduce the volume by 10%, then the loudest sound is attenuated by (65536*0.9) = 58982.4. Every 6dB of attenuation reduces bit depth by 1, so if you are listening to a 16 bit audio file and reduce the volume by 12dB, you are effectively listening to a 14 bit file. In addition to reducing bit depth, it reduces the dynamic range and worsens the signal-noise ratio. Now, you can not send a value of 58982.4 to your DAC, so Windows rounds it down to 58982 resulting in a rounding error, which is effectively quantisation noise.
Third party convolvers or high quality audio playback software does not work like that, they are able to achieve volume attenuation without introducing the problems caused by Windows volume control.
Your DAC's volume control might work by: 1. attenuating volume digitally the same way as Windows, 2. Resampling audio and then applying volume control (superior), or 3. applying volume control in the analog domain. Options 2 and 3 are better than option 1, with option 2 the best of all.
Since I do not know how your DAC works, I am unable to answer your question as to which is superior.