Treaty of Windsor
The oldest alliance in the world still in force

The 1386 treaty sealed the Anglo-Portuguese alliance of 1373 with the marriage of King John I to an English princess. The alliance has never been broken and is considered the oldest still in force anywhere.
Wikipedia (Russian) · Wikipedia (English) · 14th century
Did you know
An alliance made in the 14th century was invoked in the Second World War. In 1943 Portugal, citing its treaties with England of 1373 and 1386, let the British use bases in the Azores. Share →
Meanwhile around the world (±25 years)
Eastern Europe & Russia
- 1380 Battle of Kulikovo — 6 years earlier
- 1410 Battle of Grunwald — 24 years later
- c. 1411 Andrei Rublev's Trinity — 25 years later
Middle East
- 1402 Battle of Ankara — 16 years later
Africa
- 1377 Ibn Khaldun's Muqaddimah — 9 years earlier
Asia
- 1368 Founding of the Ming dynasty — 18 years earlier
- 1370 Timur makes Samarkand his capital — 16 years earlier
- 1377 Jikji, printed with movable metal type — 9 years earlier
- 1392 Founding of Joseon — 6 years later
- c. 1400 Founding of Malacca — 14 years later
Alive at the time
- Timur (aged 50)
- Sergius of Radonezh (aged 72)
- Murad I (aged 60)
- Ibn Khaldun (aged 54)
- Dmitry Donskoy (aged 36)
- Ashikaga Yoshimitsu (aged 28)
- Andrei Rublev (aged 26)
- Bayezid I the Thunderbolt (aged 26)
- Richard II (aged 19)
- Sigismund (aged 18)