Unexpected Victories During Medieval Battles

Can anyone tell me a battle, where a skilled ruler who outnumbered an enemy, got demolished and suffered heavy casualties?

Let’s stay focused on medieval battles.

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The Battle of Agincourt. Charles d’Albret was skilled enough I guess.

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Battle of Aljubarrota and Battle of Valverde, though arguably the Castilians were outmatched in terms of tactics in both battles, despite having much larger numbers.

The seven battles which make up the Second Siege of Cochin are also valid, with 130 Portuguese standing victorious against some 89,000 Nayars, though this was in the start of the 16th century.

Robert II of Artois got demolished at the Battle of Courtrai (1302) by an army of communal militia and armed townsfolk. While the armies were relatively even in numbers, the French were far better armed and had over 3000 knights on their side while the Flemish had none to speak of. The Flemish stoutly defended the plain outside of their city and slaughtered the superior French forces though.

Interesting…

What about any Roman defeats?

Byzantine included now…

I can only find Battle of Yarmouk and Adrianople

Battle of Montgisard: It’s a rare instance where perfect planning, numbers, good leadership defeated by bold action.

If you want a Byzantine battle, Manzikert (1071) and the Siege of Constantiniple (1204) both fit the bill.

At Manzikert, the Emperor Romanos IV (a relatively experienced Anatolian general) supposedly outnumbered the Seljuqs heavily and almost defeated them, but treachery in his own ranks combined with Turkish hit and run tactics picked the army apart and the emperor himself was captured and the army scattered to the winds.

For the siege of 1204, the Crusaders and Venetians besieged the city and were repulsed multiple times, until in one assault the Venetians captured a section of the wall. In response to this, the Byzantines marched a massive army outside the gates of Constantinople to wipe out the outnumbered Crusader siege camp. It was heavily fortified though, so the two armies essentially sat there waiting for the other to make the first move. Eventually, with the Venetians wreaking havoc elsewhere in the city, the Emperor retired with his army instead of assaulting them and then he fled in the night with the treasury (when in all likeliness he could have beat them back) and chaos ensued. The crusaders were able to place their candidate on the throne, but the infamous events leading to the sack of city were set in motion.

The only people capable of defeating the Byzantines were themselves.

The Battle of Hastings in 1066. The Anglo-Saxon King Haro is slain in battle against the Normans led by William the Conqueror, resulting in the Norman Conquest of England

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