I used iTunes Match to download about 300 songs on my iPad 2. But these songs stuck on "preparing to download" with no progress in iTunes for a couple of days. The internet connection works fine. Try restarting iPad and signing out of my apple account and back again. That's still no working. I can't also clear them.
How to fix songs "preparing to download" issue
* On your computer, deleted the songs completely from iCloud, added them back to iTunes and uploaded back to iCloud. Then you can download them from the tablet with no issue.
* You can also force iTunes match to download other material cleared the previously stuck downloads. In iTunes app, tap Purchased tab > Not on this iPad > Recent Purchases, and download some items that were not present on the device.
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