The period of the Judges covers just shy of 300 years, from the death of Joshua and the end of the generation that was born in the wilderness and conquered the land until the appointment of King Saul. Adding up the years of peace and years of oppressions seems to add up to more than that, so the years of peace and oppression given in the book must overlap some, as they were taking place at the same time in different places.
Part of the reason for this is that Israel was hardly one nation, but rather more like 12 separate tribes. Some of these tribes aren’t mentioned at all. in Judges Others are hardly mentioned after the roll call like listings of the first chapters. What affected one group did not always affect the others. The tribes took on different characters.
The accounts of judges, therefore, do not have to be in a strict chronological order. Some of these things could have been taking place in different places at the same time. To appreciate what can happen in the length of time that is covered by the book of Judges, consider a 290-year span of our history. 290 year ago, 1723, this country was only very lightly populated with a few cities on the east coast. There were 7 colonies with a population of approximately 80 thousand people in what would become the United States. St. Petersburg, Russia had just been founded by Peter the Great, and construction was just about to start at the Alamo. The industrial revolution was still 50 years off.
In Judges, we have a highly compressed account of 300 years. At the end of the book, there are two incidents recorded in great detail to illustrate how sorry a state of affairs came to exist in the Promised Land. A lot can happen in 300 years, and in Israel it obviously wasn’t all good.