How the Underdog Pulls It Off

History is littered with battles that caused unbelieving spectators to stop and stare. Often these battles were remarkable upsets where smaller armies, through skillful leadership, advantageous terrain, or plain incompetence from their enemies defeated larger foes. If you love rooting for the underdog, read how many times David slew Goliath.

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1. The Battle of Marathon (490 BCE)

Athens mustered a tiny army against the Persian invaders. Despite being hopelessly outnumbered, the Greeks charged. They attacked the Persians’ weaker center, winning through strategy and patience. The Battle of Marathon would inspire the modern marathon race.

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2. Alexander at Gaugamela (331 BCE)

The young Alexander faced a massive Persian army. Instead of folding, he punched through their center and focused on command. When their leadership was destroyed, numbers didn’t matter anymore.

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3. Hannibal’s Masterpiece at Cannae (216 BCE)

Instead of running, Rome sent every available soldier to deal with Hannibal. Cannae was beautiful, textbook warfare from Hannibal. Letting the Romans advance, he surrounded and destroyed them in a brilliant double envelopment.

Sébastien Slodtz (French, 1655–1726) on Wikimedia

4. Teutoburg Forest Ambush (9 CE)

Three Roman legions thought they had Germania outmaneuvered. Native tribes ambushed them in a vicious woodland smackdown. Rome never again attempted to expand east of the Rhine.

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5. Stirling Bridge (1297)

Like countless battles before it, English soldiers outnumbered the Scots. But instead of charging, commander William Wallace waited for the perfect moment. That patience would allow him to turn numbers against them.

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6. Bannockburn’s Mud and Spear Wall (1314)

English forces greatly outnumbered Scottish troops. Bruce’s army used tight formations and muddy terrain to counter heavy cavalry. Scotland proved itself, winning independence and major bragging rights.

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7. Agincourt and the Longbow (1415)

Among other issues, the English were sick, tired, and outnumbered. Their longbows didn’t miss, thinning the ranks of French knights slowed by disease and weather. Medieval warfare would never be the same.

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8. Caesar’s Gamble at Alesia (52 BCE)

Surrounded in a fortified town, Julius Caesar was shouldering his outnumbered warriors. Relief forces approached, and Caesar built fortifications facing both ways. He managed to win a battle on two fronts.

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9. Pharsalus and Calm Under Pressure (48 BCE)

General Pompey’s forces outnumbered Caesar’s, and had longer supply lines. Flexible troop formations and hardened soldiers would change everything. Pharsalus would signal the end of the Roman Republic.

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10. Ain Jalut Stops the Mongols (1260)

The mighty Mongol Empire had defeated anyone who resisted them. The Mamluks baited and laughed at the vaunted horde, turning their retreat into a trap. History remembers it as the Mongols’ first major loss on land.

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11. Narva’s Snowstorm Surprise (1700)

The Russian army greatly outnumbered the Swedish in troops and guns. But King Charles XII waited for low visibility in a raging blizzard to attack. When the Russians realized what was happening, it was too late.

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12. Saratoga Shifts the American Revolution (1777)

British troops hoped to crush colonial resistance with quick battles.

Things didn’t go according to plan, and ended with France entering the war. That decision would help ensure a colonial victory within years.

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13. Washington Crosses the Delaware (1776)

Thanks to costly mistakes, the Continental Army was on its back foot. George Washington sparked something in his troops by attacking the enemy at Trenton. It was only one battle, but America needed the win.

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14. Cowpens and the Elastic Defense (1781)

The British Army possessed more troops and experience fighting in the Carolinas. But a clever trap ensured that every British advantage would be turned against them. Instead of victory, they faced total collapse.

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15. Rorke’s Drift Holds the Line (1879)

Two companies of British soldiers held a supply station against thousands. Though heavily outnumbered, they made do with fortifications and relentless defense. It’s one of many examples where staying calm matters.

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16. Midway Turns the Pacific War (1942)

Japan boasted more experience and more carriers at war’s outset. But American codebreaking and bold leadership exploited weaknesses. Overnight, control of the Pacific swung in America’s favor.

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17. Dien Bien Phu Ends an Empire (1954)

The French decided that pounding an enemy fort would be a quick job. What they didn’t know was how long it took the Viet Minh to haul artillery into position. Before long, French Indochina was history.

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18. Long Tan’s Relentless Defense (1966)

One Australian company had dawned on them…they were outnumbered. Nearly the entire surrounding enemy force closed to engage them.

Individual courage and quick thinking kept them alive. By the time it was over, it was a miracle they were standing.

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19. Yi Sun-sin at Myeongnyang (1597)

Facing a Japanese fleet thousands of times larger, Admiral Yi refused to panic. Through strategy and knowledge of the terrain, he handed them one of the most impossible defeats imaginable. Knowing the terrain was crucial in this battle.

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20. Tannenberg’s Encirclement (1914)

German forces were overrun by two converging Russian armies early in WWI. Careful maneuvering and intelligence made all the difference. The Russians ended up surrounded and defeated in a very unexpected way.

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