When The Underdog Wins

History is replete with instances where small, determined forces overcame numerically (and militarily) superior enemies. Tactical brilliance, terrain mastery, morale, and even weather have flipped the odds in favor of the underdog several times throughout history. These stunning victories reshaped entire empires and historical narratives. Here are 20 unforgettable examples of the underdog getting the upper hand when it seemed impossible.

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1. Battle Of Agincourt (1415)

In 1415, English forces under Henry V faced a French army nearly four times their size. Muddy terrain and longbowmen decimated the advancing French knights. England lost only about 400 men, while France suffered up to 6,000 casualties—many from its noble class.

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2. Battle Of Marathon (490 BCE)

With fewer than 10,000 hoplites, Athens confronted a Persian invasion force twice its size. The Greeks executed a surprise flanking maneuver that collapsed the Persian center. Persian casualties soared past 6,000, while Athenian losses numbered just 192.

Georges Rochegrosse on Wikimedia

3. Battle Of Lake Trasimene (217 BCE)

Hannibal ambushed a Roman army in thick fog along Lake Trasimene, using superior positioning and surprise. Despite having fewer troops, the Carthaginians annihilated nearly all 30,000 Romans. It remains one of the largest ambushes in military history, showcasing Hannibal’s genius.

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4. Battle Of Watling Street (61 CE)

Roman Governor Gaius Suetonius Paulinus, with just 10,000 legionaries, faced Boudica’s force estimated at over 200,000. Choosing narrow terrain to neutralize the Britons' numerical advantage, the disciplined Roman formation crushed the rebellion. Over 80,000 Britons died.

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5. Battle Of Myeongnyang (1597)

Korean Admiral Yi Sun-sin commanded only 13 ships against a Japanese fleet of over 130. He exploited strong currents in the Myeongnyang Strait, funneled the Japanese into narrow waters, and sank 31 ships. His outnumbered force suffered no losses, preserving Korean naval control.

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6. Battle Of Longewala (1971)

In India’s Thar Desert, 120 Indian soldiers with jeeps held off a Pakistani armored brigade of over 2,000 men and 45 tanks. The Indians defended from fortified bunkers, coordinating with the Indian Air Force. This failed assault cost Pakistan 22 tanks.

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7. Battle Of Okehazama (1560)

Oda Nobunaga’s 3,000 men faced a 25,000-strong Imagawa force in Japan. Nobunaga launched a surprise attack during Imagawa Yoshimoto’s unguarded celebration. The enemy general was killed, his army routed, and Nobunaga began making concerted efforts to unify Japan.

Toyohara Kunichika on Wikimedia

8. Battle Of Rorke’s Drift (1879)

Just over 150 British soldiers defended a supply station against 3,000–4,000 Zulu warriors. Using tight formations, the garrison repelled multiple waves, and after 12 hours of combat, over 350 Zulus lay dead. Eleven Victoria Crosses were awarded to the brave Brits.

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9. Battle Of Midway (1942)

During WWII, the United States Navy achieved a decisive victory against the Imperial Japanese Navy at Midway. With only three aircraft carriers and around 230 aircraft, the U.S. faced four Japanese carriers and over 250 aircraft. Thanks to codebreaking and exceptional leadership, American forces sank all four Japanese carriers.

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10. Battle Of Gaugamela (331 BCE)

Alexander the Great’s 47,000 troops faced Persian King Darius III’s force of over 100,000. By using oblique formations and exploiting gaps, Alexander shattered the Persian lines and forced Darius to flee. The battle ended Achaemenid dominance and paved the way for Babylon.

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11. Battle Of Stamford Bridge (1066)

King Harold Godwinson’s English army marched 185 miles in four days to confront Viking invaders. Despite fatigue and being outnumbered, his forces surprised Harald Hardrada’s troops, who had left their armor at camp. Only about 24 ships of the Viking army’s 300 escaped.

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12. Battle Of Plassey (1757)

Robert Clive led just 3,000 East India Company troops against the Nawab of Bengal’s army of 50,000. Political manipulation and monsoon-softened terrain stalled the Nawab’s forces. Clive’s victory marked the beginning of British dominance in India, aided by the defection of key enemy commanders.

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13. Battle Of Vucji Do (1876)

Montenegrin and Herzegovinian forces, numbering around 14,000, faced a 45,000-strong Ottoman army. Choosing high ground and ambush points, they decimated the advancing enemy. Ottoman commander Selim Pasha was killed, and thousands were captured. This victory became a defining moment in Montenegro’s struggle for independence.

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14. Battle Of Chancellorsville (1863)

Confederate General Robert E. Lee divided his 60,000 troops against 130,000 Union soldiers. Stonewall Jackson’s corps executed a flanking march through dense woods. The surprise attack broke Union lines, forcing a retreat and over 17,000 Union casualties.

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15. Battle Of Ain Jalut (1260)

The Mamluks confronted a Mongol force in Palestine, despite the Mongols’ fearsome reputation and previous conquests. Through feigned retreats and ambush tactics, they defeated the invaders and captured the Mongol commander Kitbuqa. This first major Mongol defeat halted their westward expansion.

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16. Battle Of Narva (1700)

During the Great Northern War, Sweden’s Charles XII led 12,000 troops against a 40,000-strong Russian force. A sudden snowstorm blew into the Russians’ faces, allowing the Swedes to charge undetected. Russian lines collapsed in chaos, suffering over 10,000 casualties.

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17. Battle Of The Teutoburg Forest (9 CE)

Germanic leader Arminius lured three Roman legions into a dense forest under the guise of an alliance. Over several days, tribal warriors ambushed the stretched Roman column, annihilating nearly 20,000 troops. The defeat shattered Rome’s expansion east of the Rhine.

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18. Battle Of Vienna (1683)

A smaller Polish-Habsburg coalition, led by King John Sobieski, broke the siege of Vienna by a massive Ottoman army. The decisive blow came from the largest cavalry charge in history—over 18,000 winged hussars. Ottoman forces fled in disarray, abandoning artillery and treasure.

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19. Battle Of Leuthen (1757)

Frederick the Great led 36,000 Prussians against 66,000 Austrians. His forces concentrated on one flank, overwhelming the Austrians before they could realign. In the end, the Austrians lost nearly 22,000 men, solidifying Frederick’s reputation as one of history’s greatest commanders.

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20. Battle Of Tolvajarvi (1939)

During the Winter War, Finland’s Colonel Talvela led a force of 4,000 against an estimated 20,000 Soviet troops. Exploiting frozen lakes, forests, and ski mobility, Finnish troops ambushed and split the Soviet divisions. The Red Army suffered 5,000 casualties and lost 50 tanks.

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