i've had 11 songs stuck "preparing to download" on my iPad 2 for a couple of days.
unlike others (in other threads) who removed and re-added songs from their (computer iTunes) libraries, forcing iTunes to redownload the songs on their iOS devices, the 11 songs in question on my iPad were songs that are NOT available in iTunes' own database. they were either (a) my original material or (b) obscure songs i imported from CDs or LPs. that fact seemed to make the issue more difficult for me to correct.
finally, after a few hours of searching and failed attempts, i managed to solve it:
- in the iTunes app, i went to the Purchased tab.
- i selected "Not on this iPad."
- i went to "Recent Purchases" (though i suspect the particular category probably isn't critical).
- then i downloaded a couple of items that were NOT present on my device.
while the 2nd item was downloading, i suddenly got a pop-up that said "11 items could not be downloaded at this time. Please try again later" (or something like that). and at the same time, that annoying red badge with the numeral 11 disappeared from the Downloads icon.
in short, forcing itunes match to download other material cleared the previously stuck downloads.
i hope this works for someone else.