Assuming that it is actually using the date/time rather than the physical order you could use the old UNIX favorite
touch to set the dates of files and/or directories, a collection of windows versions of some of the most used Unix/Linux command line tools is MSYS.
Since it looks like that will not work on some media players, as they use the FAT entry order, you could use python with the construct library and the excellent v-fat shuffler script written by Mike Kazantsev as described in his blog and released on github.
A couple of words of caution
- As far as I can see the script referenced above should work nicely but I don't have your media player to try it on ....
- Unplugging your player before the script is finished might leave you with a corrupted FAT, i.e. a broken player.
- You will need to install Python 2 - 32 bits from here - It is free.
- You will also need the construct library installed - pip install construct - also free.
- Download the code and try it.
Downloadable Executable of V-FAT Shuffler
To save installing all of the above I have used py2exe to build the above into an executable and have placed the zip on my Google Drive this zip file includes the Microsoft Visual C++ Redistributable that you will probably need, the source code and a dist directory which you should be able to use.
You can get instructions on how to use by running, in the dist directory:
I have had very limited time to test this so if it works for you please let me know.