I am having exactly this problem with a an epub I'm putting together. I have put the publication together in Sigil. I've added the font and it appears just fine in Sigil and Calibre's viewer. However it fails to display in ADE and on my Sony 650.
Note that in the epub the opf is in the OEBPS directory and the Font directory is a subdirectory in that. In my particular case the line in the opf file is:
<item href="Fonts/Math2%20Regular.ttf" id="Math2Regular.ttf" media-type="application/x-font-ttf" />
This is correct since Fonts is a subdirectory of OEBPS. "../Fonts/Math2%20Regular.ttf" would place the Fonts directory off the root directory of the epub.
I've had this happen on a few occasions and I am at a loss as to understanding why. The CSS seems to be correct and all the rest of the formatting in CSS works. If it would be helpful I could post the entire CSS file.
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