Anglo-Portuguese Treaty of 1373
The Anglo-Portuguese Treaty of 1373 was signed on 16 June 1373 between King Edward III of England and King Ferdinand I and Queen Leonor of Portugal. It established a treaty of "perpetual friendships, unions [and] alliances" between the two seafaring states, and remains the longest-standing treaty still in effect today.
Source: Wikipedia — Anglo-Portuguese Treaty of 1373 (CC BY-SA 4.0)