Random Worst Defeats in Military History (17 items)

(#10) Spanish Armada

The destruction of the Spanish Armada is one of the greatest naval defeats of all time. The Spanish amassed a massive fleet, under the command of the Duke of Medina Sidonia, to conquer Britain. The outnumbered and outgunned Brits, led by Sir Francis Drake, took advantage of the large Spanish vessels, which lacked maneuverability. Drake's forces used fire ships, or ships loaded with explosives, lit on fire, and sent at the enemy.

Forced to retreat under a fusillade of fire ships it couldn't evade, the Spanish Armada was destroyed by a storm on its way back to Spain.
(#1) Battle of Cannae
- Roman Italy, Italy
The Battle of Cannae was fought between the forces of Rome and Carthage, the latter led by Hannibal. Hoping for a decisive victory over Hannibal, Rome sent a massive force after the Carthaginian army. Outnumbered, Hannibal drew the Romans in with a retreating line of men, before flanking them with spearmen. A cavalry charge from the rear surrounded the Romans, and the army of Carthage devastated them.

The Battle of Cannae is known as the greatest defeat in Roman history, and one of the great strategic coups in history. As many as 70,000 Roman soldiers were lost in the battle.
(#4) Battle of the Teutoburg Forest
- Osnabrück, Germany
Known as one of the worst defeats in Roman history, the Battle of Teutoburg Forest was waged between the Germanic forces of nobleman Arminius and three legions of Rome. The unsuspecting Romans were ambushed by the Germanic force, which hid among trees in the dense forest. The Germans surrounded the Romans and stormed them.

Arminius received a Roman military education in his youth, and was able to use Roman strategy against the Legions. Publius Quinctilius Varus, commander of Rome's men, ended his life in the wake of the battle.
(#9) Battle of Agincourt
- Azincourt, France
The Battle of Agincourt was a major engagement in the conflict that raged for a hundred years between England and France, famously dramatized by William Shakespeare in Henry V with the St Crispin's Day Speech.

The English, led by King Henry V, were less than 6,000 strong, and trying to retreat from enemy territory when blocked by a French army of 20,000. When the French advanced slowly in their heavy armor, the English used the superior range of their longbows for distant combat. Even the French cavalry couldn't outflank the English when fired on by their archers. In the end, about 6,000 Frenchmen were lost, while Henry only lost 400 men.

The Battle of Agincourt is known as one of the greatest victories in military history. But in every great victory, there's a loser's worst defeat.
(#15) Battle of Actium
- Ionian Sea
The Battle of Actium was one of the few naval engagements in Roman history, fought during the civil dispute between Octavian and Mark Antony. An early advantage by Octavian caused Cleopatra, Antony's Egyptian lover, to flee the battle. Antony abandoned his post and followed her. Their commanders gone, Antony's men surrendered to Octavian.
(#12) Napoleon's Invasion of Russia (1812 CE)

Feeding off the momentum from the conquest of most of Europe, Napoleon Bonaparte set his sights on Russia. Russian forces retreated as the French advanced, biding their time for winter. When the cold weather set in, the Russians began their operation. Unfamiliar with the harsh cold and bewildered by the Russians' style of combat, French forces were worn down, and forced to pull out of Russia altogether. Napoleon's reputation and power base never recovered.