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The Second Attack on Hanthawaddy and the Siege of Toungoo, 1599–1600
Towards the end of King Nanda Bayin's reign, the kingdom of Hanthawaddy broke apart. Toungoo and Arakan rebelled, and had earlier approached Ayutthaya seeking an alliance. Naresuan marched out once more, but when he reached Hanthawaddy the city had already been burned and abandoned, so he pressed on to besiege Toungoo, deep in the interior of Burma.
The ≈ sign marks an approximate location. Borders on the map are modern and shown for orientation only. Campaign routes are approximate lines drawn from the chronicles and modern studies, not the exact path taken. Dashed lines are enemy armies.
An ally turns traitor
As an English-language encyclopedia summarises it, the King of Toungoo feared that if Ayutthaya took Hanthawaddy, Toungoo would end up as a Siamese vassal too. So he joined forces with Arakan to seize Hanthawaddy for themselves, and stirred up the Mon along the Tenasserim coast to cause unrest and hold up the Thai army.
Hanthawaddy in flames
The Thai chronicles say Naresuan first had to put down the Mon at Martaban before marching on Hanthawaddy. When he arrived, he found that the King of Toungoo and the Arakanese army had already taken King Nanda Bayin off to Toungoo.
Before leaving, the soldiers of both armies plundered the city and set fire to the palace and the monasteries. The once-great capital of Hanthawaddy was left an empty city with fires still burning.
The siege of Toungoo
Naresuan followed and laid siege to Toungoo, about 180 kilometres north of Hanthawaddy as the crow flies. He tried to drain the city moat so that he could attack. Some Thai documents say he had a canal dug to link the moat with the river, which later became known as Khlong Ayothaya (the Ayutthaya Canal).
The siege lasted about two months, but the Thai army ran short of supplies, because it was far from home and Arakanese guerrillas kept raiding its supply convoys. In May 1600 Naresuan withdrew.
The end of King Nanda Bayin
In December 1600 Natshinnaung, the eldest son of the King of Toungoo, killed King Nanda Bayin at Toungoo, and the First Toungoo dynasty came to an end.
Later, King Nyaungyan, King Nanda Bayin's younger brother, who had not been caught up in the turmoil at Hanthawaddy, established himself at Ava and founded a new dynasty in 1603. This King of Ava was Naresuan's last adversary.
The furthest into Burma
The Toungoo campaign took Ayutthaya's armies further into the interior of Burma than at any other time in Naresuan's reign. Silpa Wattanatham magazine even calls him the only Thai king to lead an army deep into inner Burma.
Reading the route on the map
The line on the map runs from Ayutthaya through Martaban and Hanthawaddy to Toungoo. The sources used do not name the pass across the Tenasserim Hills or the route of the retreat, so the first stretch shows only the general direction.
Waypoints along the route
| Waypoint | Coordinates | Notes |
|---|---|---|
| 1. Ayutthaya | 14.348, 100.561 | |
| 2. Martaban (Mon revolt crushed) | 16.530, 97.602 | |
| 3. Hanthawaddy (burned and deserted) | 17.337, 96.480 | |
| 4. Toungoo | 18.933, 96.433 |
Where historians still disagree
- Year of the campaign: Thai sources use BE 2142–2143, and some date the siege of Toungoo to BE 2143. English-language works use 1599–1600 and say the army withdrew in May 1600.
- Length and method of the siege: the encyclopedia says the siege lasted about two months and involved draining the moat. Some Thai documents say it ran from March to April and mention the digging of a canal called Khlong Ayothaya.
- Who fought alongside the Thai army: some encyclopedias say the ruler of Chiang Mai was among the Thai army's allies at Toungoo, but the details are still unclear.
Frequently asked questions
Why did Naresuan fail to take Toungoo?
Because the Thai army was very far from home, short of supplies, and had its supply convoys raided by Arakanese guerrillas. After a siege of about two months it had to withdraw in May 1600.
Who burned Hanthawaddy?
The armies of the King of Toungoo and of Arakan, which took Hanthawaddy before the Thai army got there, then plundered it and burned the palace and monasteries before taking King Nanda Bayin away to Toungoo.
- Burmese–Siamese War (1593–1600) - Wikipedia
- Naresuan - Wikipedia
- Learning Materials on the Life of King Naresuan the Great – Naresuan University (in Thai)
- Biography of King Naresuan the Great – TruePlookpanya (in Thai)
- “King Naresuan”: The Only Thai King to Lead an Army Deep into Inner Burma – Silpa Wattanatham (in Thai)
- Taungoo - Wikipedia
Last updated 10 November 2026