If your using Windows Media Player, you may have to do the following (I use WMP and directly uploading).
Make sure all ID3 tags are set correctly
-This is if your doing albums-
As long as it shows the track, album and artist the way they should be, you should have little to no problem getting them to play in order.
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I've never seen a MP3 player that you can select the order in which multiple songs are played, unless you do it manually or only have the song you want to play on it.
I think your efforts will be in vane. Sorry
This is from Memorex FAQs:
Some programs put the track number as the first 2 characters of the song title (file name) this will cause the player to put the songs in the same order as the CD (or album for those of us old folks). If you drag files onto the MP3 players you can arrange them in any order you wish in the file view of your windows computer. When you go through the songs on the MP3 player, they will be in alphabetic order based on the file name (song title usually). You can't change the player's settings to play in anything but alphabetical order. There is a work around: People can force the play list order by naming the songs with a numeric prefix (i.e. 01, 02 etc) so the alphabetic listing in the player will put them in the order you prefer.
I used ID3-TagIT to change the album name of my songs to the name of the folder on my Sansa c250 that I want to put the songs in. Open your Sansa in My Computer, double click on Internal Memory and open the music folder. Add a new folder and name it whatever you put in for the album name of your songs. Highlight all your songs and drag and drop them into your folder. Don't use media player to sync or they end up all mixed up in different folders.