No-one maintains the Pascal support in GDB. In fact, I think the test suite doesn't even run any more (at least for me, FPC seems totally broken). This is an area where a volunteer could make useful progress pretty easily.
On linux it works fine, on windows it sucks but there are some workarounds to make it usable : https://wiki.freepascal.org/Debugger_Setup
Unfortunately, I use Pascal and there it is even worse
GDB tries to parse Pascal syntax in print, but many expressions do not work. It is almost a mix of Pascal and C.
The integration in the Lazarus IDE makes it even worse, when you cannot enter all expressions. And there are so many bugs. You get GDB crashing, Lazarus crashing, or GDB freezing the entire X server if it pauses the program in a bad moment. Then you need to restart the system or kill GDB from outside the X server.