First, copy the font into the correct location in the bottle. This would be __~/.cxoffice/(bottlename)/drive_c/windows/fonts__.
Then run
~/cxoffice/bin/wine --bottle (bottlename) --untrusted --wait-children -- cxinstallfonts.exe ~/.cxoffice/(bottlename)/drive_c/windows/fonts/(font name)
Replace (bottlename) with the name of the bottle you've installed the font into. You may also have installed the Crossover binaries into /opt/cxoffice instead of ~/cxoffice.
Other Articles
How to manually change file associations in a bottle.
How do I map a drive?
How can you map a document type to open in a native application?
Enabling subpixel rendering/anti-aliasing in CrossOver.