There are cases - for example, the American Revolution. George Washington's army lost just about every battle with the British, who had a much better army. The war was basically won by guerrilla forces that managed to undermine the British occupation.
There are very interesting books about these events, for instance one by a very well-known American historian named William R. Polk called Violent Politics. It's a record of what are basically guerrilla wars from the American Revolution right up through the wars in Afghanistan and Iraq.
The American Revolution was a small part of a major world war going on between France and England, so the French intervened and that was a big factor, but the domestic contribution was basically guerrilla warfare.
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