Does anyone remember Redhooks Revenge? It was a maritime-themed trivia board game with risk battle mechanics for DOS. You can see the original here:
https://archive.org/details/RedhooksRevenge
I actually received permission from ImagiSOFT to build the sequel, titled Redhook's Revenge: Call of Booty which adds in 1000s of general trivia questions, which is freely available on itch.io:
https://specularrealms.itch.io/redhooks-revenge-ii-call-of-b...