Anglo-Portuguese Alliance
The Anglo-Portuguese Alliance (Portuguese: Aliança Luso-Inglesa, "Luso-English Alliance") is the oldest alliance that is still in force by political bilateral agreement. It was established by the Treaty of Windsor in 1386, between the Kingdom of England (since succeeded by the United Kingdom) and the Kingdom of Portugal (now the Portuguese Republic).
Source: Wikipedia — Anglo-Portuguese Alliance (CC BY-SA 4.0)