I know a bit about fonts … and it's a little complex. There's not much overlap between a stock Raspberry Pi and Windows in the font department. Microsoft pays a lot of money to develop typography, the Raspberry Pi Foundation uses whatever it can get.
The list of fonts installed on a stock Raspberry Pi/Raspbian is:
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DejaVu Math TeX Gyre
DejaVu Sans
DejaVu Sans Condensed
DejaVu Sans Light
DejaVu Sans Mono
DejaVu Serif
DejaVu Serif Condensed
Droid Sans Fallback
FreeMono
FreeSans
FreeSerif
Lato
Lato Black
Lato Hairline
Lato Heavy
Lato Light
Lato Medium
Lato Semibold
Lato Thin
Liberation Mono
Liberation Sans
Liberation Serif
Noto Mono
OpenSymbol
Piboto
Piboto Condensed
Piboto Light
PibotoLt
Piboto Thin
Short of installing Gnome Font Viewer, the easiest way to get the installed list is this snappy little number:
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fc-list | awk -F: '{sub(/^ /,"",$2); split($2, variants, /,/); for (i in variants) {print variants[i];}}' | sort -u
The Raspberry Pi's font handler can quietly substitute for certain fonts. If you install Carlito, then ask for Calibri in your program, you
should get Carlito without explicitly asking for it.
There are many reasons that fonts won't look dot-for-dot identical across platforms. Windows' Courier is different from Apple's. Apple's Helvetica tends to be Helvetica Neue. For cleanest results, install open-licensed fonts everywhere, such as Google Roboto, Google Noto, IBM Plex, Inconsolata, Courier Prime, …
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