What about using SVG instead of fonts? Not sure below collection has 'loop once' icon but worth checking it out.
thenounproject.com

Also I think Itunes' 'loop once' icon is done with '1' in a circle right?
www.alanwood.net/demos/wingdings-2.html go down to 'J' or 'U'

You might try to overlay the 'circled 1' with CSS on top of your loop icon.

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: Looking for font with music player controls: loop all, loop once, shuffle Any suggestions? I searched FontSpring, FontSquirrel, and MyFonts to no avail.

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