Military History: 10 Amazing Military Underdog Stories

Underdogs have a special place in the hearts of many, whether it’s the upstart Celtic Iceni tribe led by Boudicca revolting against the Romans or the ice-veined Spartans fighting in one of history’s greatest last stands against the Persians at Thermopylae. Either through superior tactics or more technologically advanced weaponry, the outnumbered often achieve some form of victory, whether moral or outright. Here are 10 such examples of great historical underdogs.


10. British East India Company, Battle Of Assaye


Arthur Wellesley, the major general of the British forces and future first Duke of Wellington, said this of the battle: It was “the bloodiest for the number that I ever saw.” One of the major battles of the Second Anglo-Maratha War, a conflict between the British East India Company and the Maratha Empire, the Battle of Assaye saw between 6,500–10,000 British soldiers face off against a 40,000–50,000 strong Maratha army.

Unfortunately for the British, their intelligence about the strength and location of their enemy was flawed. Not only were they in the wrong location, but they were much stronger than expected, having recently swelled by several divisions. Luckily for Wellesley, he was a better battlefield general than he was a strategist, as he quickly devised a plan to strike quickly, rather than wait for the reinforcements coming along under the command of Colonel Stevenson. (He had divided his army based on the faulty intelligence he had received, and the rest of his forces were miles away.)

However, the main reason for the British victory was the Maratha army simply didn’t believe that Wellesley would attack while being outnumbered so badly. This surprise led to a rout, one in which 5,000–6,500 soldiers of the Maratha army fell in battle. (The British lost about 1,500.) Later in his life, the Duke of Wellington reminisced about his many military triumphs and concluded that his victory at Assaye was the greatest of them all.

9. King David IV And The Georgian Army, Battle Of Didgori


Otherwise known as David the Builder for his role as the architect of the Georgian Golden Age, King David IV of Georgia (the country, not the state) was faced with a problem that had plagued his country for years. The Seljuq Turks, Muslims from present-day Kazakhstan, had control over most of the Georgian state. (Various internal wars and earthquakes also helped to weaken the country’s resolve.) Ascending to the throne at the tender age of 16, David IV gathered together the various feudal lords in the area, formed an army, and began repelling the Seljuq occupiers, refusing to pay them any tribute.

Invigorated by the First Crusade’s success against Muslim armies, David IV initiated his plan to take Tbilisi, a great Georgian city and future capital of the country, which had been under Muslim control for nearly 500 years. So around 56,000 men began marching toward the city, camping at Mount Didgori, some 40 milometers (25 mi) from Tbilisi. Though contemporary records exaggerate the amount of forces facing the Georgians, conservative estimates put it at 100,000–250,000 men.

In a similar vein to Stalin and his infamous Order No. 227 (the “Not one step back!” order), David IV declared that retreat was not an option, barricading the route behind his men with trees and boulders. Then, in an act of treachery, he sent 200 heavily armed cavalrymen to the Seljuq leaders under the pretense that they were deserters. When they arrived, the Georgians attacked, killing the leaders and demoralizing the Muslim army. The Battle of Didgori was on, and it only lasted three hours, with the Seljuq Turks taking heavy losses, both as dead and captured, while the Georgians got off relatively light. (Actual casualty counts are hard to come by.) Tbilisi soon fell, and Georgia had its capital once again.

8. Mexican Army, Battle Of Puebla



Picture it: Puebla, Mexico, 1862. The liberal Benito Juarez had been elected as president during the prior year, as the country began to fall into financial ruin, thanks to the enormous foreign debt they had accumulated over the years. Britain, France, and Spain each sent their own navies to Veracruz, demanding payment from the Mexican government. Deals were reached with Britain and Spain, who departed shortly afterward, but Napoleon III, nephew of Napoleon Bonaparte, saw an opportunity to establish a Mexican empire and refused to negotiate, landing an invading army instead.

Veracruz was stormed first, quite successfully, and the ease of the fighting convinced the French leaders that victory would come quickly throughout the country. Mexico City, the capital of the country, was the target, but a well-fortified city lay in the direct path the French decided to take: the city of Puebla. 6,000 French troops marched on the city, determined to wrest it from the hands of its ragtag band of 2,000 men. (As any military historian would tell you, a ratio of at least 3:1 is necessary for any sieging army.)

However, even with their superior numbers and artillery, the French were rebuffed in their assault. Starting at daybreak on May 5, the fighting lasted until early evening, with the French suffering five times as many casualties as the Mexicans. (Admittedly, the French only lost 500 people.) It was not strategically important—not only did the French ultimately take over the country for a short period, they even took the city itself a year later. But the victory served as a morale boost for the Mexican army, as well as the people of Mexico, who later created a holiday to celebrate the battle: Cinco de Mayo. (However, it is much more widely celebrated in the United States today than anywhere in Mexico, often under the misnomer of Mexican Independence Day.)

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