The history found in chapter 2 of Judges is an undeniable case study of the faithfulness of God to his Word, especially as it relates to the book of Deuteronomy. This paper, with great brevity, will look at the numerous connections Judges 2 has with the whole of the book of Deuteronomy. The richness of the interconnectivity demonstrates how these are not two unrelated books, but rather essential components of redemptive history that are meant to depend on one another. This will be demonstrated by first taking a broad look at the connections between the covenant curses and blessings of Deuteronomy 28-30 with Judges 2, and then focusing more specifically on the fulfillment of warnings and promises made in Deuteronomy in connection to failing to destroy the Canaanites, violating the covenant through idolatry, the role of judges/leaders, as well as divine testing and repentance.