5. Siege of Drepana – 249 – 241 BC
Taking place during the First Punic War, Drepana was a naval stronghold for the Carthaginian forces. The Carthaginian forces put up a strong fight, even managing to destroy the Roman naval blockade, allowing support to make its way to the besieged port. But the Romans returned with a rebuilt fleet and destroyed the Carthaginian fleet, ending the War and the Siege after eight years.
4. Siege of Thessalonica 1422 – 1430
When the Byzantine Palaiologoi dynasty attempted to incite rebellion amongst the Ottoman army, the Ottoman Sultan responded by launching an assault on the city of Thessalonica. Despite their lack of supplies, the Venetians managed to hold out against the Ottomans for eight years before the city was finally taken and subjected to three days of pillage and destruction.
3. Siege of Ishiyama Honganji 1570 – 1580
Fought between the warlord Oda Nobunaga and the Ikkō-ikki monks in modern day Japan, the Siege was Oda’s attempt to defeat the network of fortifications belonging to the monks. After building fortresses, attempting to starve the Ikki as well as frontal attacks, Oda finally brought the Ikki to the negotiations table when their supplies and allies were all but spent, an incredible 10 years after the siege began.
2. Fall of Philadelphia 1378 – 1390
When the Byzantine civil war turned disastrous, the Emperor Manuel II Palaiologos promised the city of Philadelphia to the Turks. However, the residents of Philadelphia were not so keen on this idea and managed to resist the invaders for an impressive 12 years before the city was finally taken by the Turkish forces.
1. Siege of Candia 1648 – 1669
Taking place in the 17th Century, the Seige of Candia was a conflict between the Ottoman Empire and the Venetian ruled city. After the Knights of Malta attacked an Ottoman convoy, the Ottoman’s responded by sending 60,000 troops to Candia, where the Knights had landed with the loot. Although the Ottoman forces were ultimately successful, the Venetians held out for a massive 22 years, making it the longest siege in history.