https://bugs.winehq.org/show_bug.cgi?id=44065
--- Comment #20 from Peter Beutner p.beutner@gmx.net --- (In reply to Fabian Maurer from comment #19)
There is nothing fixed in wine, and it should work with worms2.exe too.
there is nothing to be fixed in wine. see the details from the bug i linked earlier.
when you start worms2.exe directly it reads Data\land.dat to know which level to load. While frontend.exe allows you to choose a level, then calls landgen.exe which modifies Data\land.dat to point to the correct level, and then launches worms2.exe
The problem is that the GOG ships a Data\land.dat which points to a level in 'c:\nw2'. Which normally doesn't exist (unless by chance you installed worms into that path). That's why launching worms2.exe produces an error.
if you launch frontend.exe first, it will write the correct path into land.dat and the game starts up fine. subsequent launches via worms2.exe should actually work after the first one.
if anything this is a GOG packaging bug. But since you normally run the game via frontend.exe it is a rather obscure corner case