1)double check if the ttf in is your resource folder

2) check spelling e.g

"10"
{
"font" "resource/fonts/wingdings2.ttf" <-the spelling is for word
"name" "Wingdings 2" <-the spelling for this two. preview or install to check
}

3) im not sure how it'll affect the thickness of fonts such as wingdings but you have set most of the fonts using wingdings 2 or webdings to 0. try setting it to something higher to see if thickness is an issue.

4) font size could also cos some letters ,or symbols in this case, to disappear as they're too small to be seen.

Not sure if this will help you solve your problem but its worth a try

if u could link me the specific ttf for both wingdings 2 and webdings, ill see if it works for me or not.

3. Thickness shouldn't be an issue, as I mentioned other fonts display fine.

4. The characters do, in fact, show, but they are characters from one of the default Fonts, and not Webdings/Wingdings. Therefore I assume sizes are not the issue.

I copied the Webdings/Windings 2 files straight from the Windows Fonts folder, but here they are (including AlternativeGothicEF-NoThree and Guifx v2 Transports): http://www.mediafire.com/download/5qgjhwl8wbiikmr/fonts.rar

i just used it and the font becomes the default ttf. I digged into the wingdings 2ttf using fontcreator and realised that wingdings 2 had no abcd etc equivalent.

I googled and found out that the only way to add them into word was by using the the menu item insert or alt codes. Unless you can do this for tf2, I dont think its possible to use either fonts for your hud

That seems strange. By default, both fonts are installed on Windows systems and usable in Microsoft software like Word. I would have thought that if the fonts didn't have glyphs for alphabetical character inputs, you wouldn't see anything when using it in Word.

Since Guifx seems to work, would it be possible to port some of the characters from Webdings/Wingdings 2 into the Guifx font? Namely, the trophy (Webdings %) and the left/right half circles (Wingdings 2 º »).

its possible. just need to extract the images u want and port over to another ttf using a font editor.

Alright, I was able to import the needed characters into another .ttf in FontForge. However, I need to use it with a "tall" value of 320; for some reason, it won't let me use anything above 80. Is there any way around this?

I have a suggestion, this us just an alternative to the font, you could always look into Font Awesome, very good series of well known and generic icons.

http://fortawesome.github.io/Font-Awesome/

But I have no idea how you would get them to work inside of TF2.

I don't think I need these icons to be honest.

I have never worked with such a tall value for any of my fonts before as I dont need to. Sorry but Im afraid Ill not be much help to you on that particular matter.