Duchy of Nassau
They engaged the French on many occasions, clearly capable of standing up to the French however they were ultimately deafened after an engagement at the town of Smohain and the farm of Frichermont, they became part of the Confederation of the Rhine, Ending their independence, they were annexed by Prussia and became an independent state. Later, Nassau helped in the Battle of Waterloo before being absorbed into the Prussian Empire, and later, the empire of Germany.