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Top 10 Most Important Medieval Battles and Sieges
Find out about 10 of history’s most iconic medieval battles.

Mar 2, 2022 • By Chester Ollivier, BA (Hons) History
siege antioch battle sluys and agincourt illustrations

The medieval period, sometimes referred to as the Middle Ages, was the
period that spanned just over a millennium from approximately 300 CE to
1500. During this period the world was transformed, and some of the most
famous battles in history took place in this era. There is not one
factor which characterizes a medieval battle or siege, as warfare
evolved over the centuries. This article will not simply describe the
types of warfare, it will explain the results and what they meant for
the medieval world.

1. The Dawn of the Middle Ages: The Medieval Battle For Rome, 24th
August 410

sack of rome sylvestre
Sack of Rome by the Visigoths on 24 August 410, by Joseph-Noël
Sylvestre, 1890, via Wikimedia Commons

A common misconception about the “Middle Ages” or “medieval” world is
that it was all knights in shining armour, chivalry, and ladies in
waiting. Part of it was — the period known as the “High Middle Ages”,
which spans from around 1000-1300 — but the reality is that the early
medieval period set the precedent for the High Middle Ages. One of the
most famous medieval battles is the Sack of Rome, conducted by Alaric
and his Visigoths in 410 CE.

For some time, the Roman Empire had been heading towards collapse.
Events during the Third Century Crisis which had been partially
rectified by Emperor Diocletian still stung the Roman population almost
two hundred years later. A disgruntled populace was there for the taking
when heavily armed enemies were outside the very walls of Rome.

thomas cole course of destruction painting
Course of Destruction, by Thomas Cole, 1836, via Google Arts & Culture

After besieging the city for weeks, the Visigoths devised a plan whereby
they would offer the Romans in the city some of their slaves, out of a
mark of respect for withstanding a siege for so long. Sure enough, the
Romans opened up the Salarian Gate, and the Visigoths poured into the city.

Alaric and his Visigoths besieged Rome for three whole days, murdering
aristocrats, burning buildings, and looting anything they could get
their hands on. In the space of three days, the ancient city of Rome —
which had not been sacked for over 800 years — had been completely
ruined within the space of three days. To make matters worse, the Romans
viewed the Visigoths as barbarians, or savages, and themselves as superior.

The reason that this medieval battle makes the list is because of the
impact it had not just on Rome itself, but on Roman thinking: they had
been completely obliterated by an army of savages. They realised that
they were not immortal, and their city was in fact penetrable. The
Visigoths had certainly played their part in ensuring its quick demise
after the Sack of Rome in 410.

2. The Battle For England: The Battle of Hastings, 14th October 1066

bayeux tapestry medieval battle
Section from the Bayeux Tapestry, c.1070, via Culturetrip.com

This next medieval battle is one that almost everybody has heard of. It
marked the end of Saxon rule in England, and the beginning of Norman
rule. The battle was so significant because the Royal Family in England
can be traced back over 1000 years to the Battle of Hastings, where the
Norman Dynasty were the victors and their descendants were to rule
England for over 1000 years.

The battle itself took place on the South-East coast of England in a
town called Hastings. The English king at the time, Harold II, had just
finished a battle at York and his troops marched down the country at an
extraordinary speed to meet with William of Normandy’s forces. Harold’s
troops were exhausted from the demanding march after days of fighting
over 300 miles away, and they were already at a disadvantage because of
this.

William’s forces took advantage of this and won a decisive victory, with
Harold II being killed, allegedly by an arrow that was shot into his
eye; an image which is depicted in the famous Bayeux Tapestry. William
was crowned as William I of England on Christmas Day 1066, and today is
better known by his eponym: William the Conqueror.

3. The Battle of Antioch, 28th June 1098

sieg of antioch drawing
The Siege of Antioch, from Sébastien Mamerot’s Les Passages d’Outremer,
c. 1474, via thegreatcoursedaily.com

The Battle of Antioch was part of the conflict known as the First
Crusade, in which Christian European forces rallied together after Pope
Urban II’s famous Council at Clermont in 1095 to aid their Byzantine
brethren in the East against Muslim forces.

After fighting at Nicaea and Dorylaeum, the Crusaders reached Antioch.
Their goal was to take Jerusalem (which they were eventually successful
at — to an extent), so why has the victory at Antioch been included in
this list of medieval battles?

For a start, where Antioch was situated was key for the Crusaders. It
was located in present-day Antakya, Turkey, east of the Orontes River.
This meant that supplies could be shipped from Europe, and through the
river systems of Greece and Turkey to reach the Crusaders. In addition,
the Battle of Antioch was the culmination of what became known as the
Siege of Antioch: an eight-month long siege of the city, which lasted
from October 1097 to June 1098.

The Christians had to defend Antioch, or all of their attempts to reach
Jerusalem — the Holy Land — would have been in vain. Eventually, six
divisions of the starving Christian troops emerged from the gates. The
Muslim leader, Kerbogha, ordered an immediate attack, but Bohemond of
Taranto — a Crusader leader — had planned for this, and a seventh
division of Christian soldiers managed to hold off the attack.

The Crusaders allegedly saw visions of St George which boosted their
morale, and eventually, the Muslim troops retreated, scattered in
numerous different directions and the Crusaders kept hold of their
precious city of Antioch.

4. The Fall of Jerusalem: The Battle of Hattin, 4th July 1187

hattin medieval battle manuscript
The Battle of Hattin, from Chronica Majora, by Matthew Paris, 13th
century, via the Metropolitan Museum of Art

Another battle from the Crusades makes this list of greatest medieval
battles. Yet this time the battle was not a victory in favor of the
Crusaders. After the Second Crusade — a disaster for the Crusaders — the
troops were faced with one of the Islamic world’s most formidable
military leaders: Al-Nasir Salah al-Din Yusuf ibn Ayyub, better known as
Saladin.

Saladin’s Muslim troops had positioned themselves carefully, in an arc
shape around Hattin, which cut off the water supply from Lake Tiberias
(known today as the Sea of Galilee). This not only ensured that the
Muslim troops could stay hydrated for as long as necessary, but it made
the Crusaders dehydrated and thus weaker.

The Muslims surrounded the Crusaders overnight, keeping them awake by
chanting prayers and beating drums. They also set fire to the dry grass
around the Crusader camp, which made their throats even drier.

On the morning of July 4th, the Crusader army was blinded by smoke from
the Muslim fires, which gave the Muslims the perfect excuse to open fire
with their archers. Thoroughly demoralized and disorientated, the
Crusaders broke formation and made for the springs of Hattin. However,
due to dehydration and their injuries, the vast majority of them were
simply picked off by Muslim soldiers and killed. Saladin had
successfully taken back Muslim lands, which is why this is one of
history’s greatest medieval battles.

5. Battle of Bouvines, 27th July 1214

battle of bouvines medieval battle
The Battle of Bouvines, 1214, by Horace Vernet, 1827, via Fine Art America

In 1212, King Philip II of France had planned to cross the English
Channel and take England for himself. This had scared the English king,
King John, enough to realize how vulnerable he was with less than 30
miles of water between the two feuding kingdoms.

As a response, John made peace with the Church (he had been effectively
placed under suspension by Pope Innocent III in 1208 for his constant
arguing with the Church). This came at a cost, though: he promised to
surrender his kingdom to the Pope as well as to pay an annual sum of
1000 marks to Innocent and his successors in perpetuity. A
fourteenth-century chronicler, Henry Knighton, noted that John had
“turned himself from a free man into a slave”.

As a result, John had no option but to go to war, and his forces (along
with those of the Holy Roman Empire under Otto IV) met at Bouvines. The
Allied army of 9,000 outnumbered Philip’s army by 2000. Nevertheless,
the French army destroyed John’s forces and completely destroyed any
hopes of John regaining his territory.

This was a hugely significant medieval battle for a number of reasons:
firstly, it signified the early collapse of the Plantagenet Empire — all
of the territory that had been won under John’s father, Henry II, was
now lost. Secondly, it ended the Anglo-French war of 1213-14. Thirdly,
it changed the course of English history forever. Realizing how weakened
he was, John’s barons forced him to sign the Magna Carta, a legal
document that still holds precedent in English law over 800 years later.

6. The War for Scotland: The Battle of Bannockburn, 24th June 1314

battle bannockburn illustration
The Battle of Bannockburn, from Walter Bower’s Scotichronicon, c.
1440s, via themedievalists.net

One hundred years after Bouvines and during the reign of King John’s
great-grandson Edward II comes another one of history’s greatest
medieval battles: the Battle of Bannockburn.

Bannockburn was part of the Anglo-Scottish wars which stretched from the
late thirteenth to the mid-fourteenth centuries. The Scottish king,
Robert I (better known as Robert the Bruce) had reclaimed both Roxburgh
Castle and Edinburgh Castle in early 1314, which essentially invited the
English to war in Scotland.

The resulting confrontation was the Battle of Bannockburn, which was one
of the most catastrophic defeats in English history. It was a disaster
before the battle had even begun: the English Earls of Gloucester and
Hereford argued over who should lead the vanguard, and Edward accused
the Earl of Gloucester of being a coward — not ideal in the hours before
a battle.

Enraged by the king’s comments, Gloucester charged forward to meet the
Scottish forces and was killed. The Scottish army then forced the
English back into the Bannockburn stream and trapped it in between the
riverbanks, the English forces lost formation and broke ranks.

To rub salt into English wounds, it is estimated that Bruce’s Scottish
forces only numbered 6,000, compared to Edward’s army of 20,000. Such a
huge military disaster tainted Edward II’s reputation as king,
particularly given that his father, Edward I, was so successful against
the Scots. To make matters worse posthumously for Edward II, his son,
Edward III, was also successful against the Scots on numerous occasions,
making Edward II’s reputation even worse. And it is Edward III who we
turn to next.

7. The Battle of Sluys, 24th June 1340

battle sluys illustration
The Battle of Sluys, from the Chroniques de Jean Froissart, 15th
century, via Bibliothèque Nationale de France

So far, all of the battles that have been discussed have been
land-based. Sluys was different: it was a naval battle. Part of the
Hundred Years War (1337-1453), the battle of Sluys was one of Edward
III’s most notable victories and a huge victory for England. With King
Philip VI of France having his attention set on the North Sea in early
1340, Edward III knew he had to act to defend his kingdom. However, the
odds were instead in Philip’s favor: by June, he had amassed a fleet of
213 ships, while Edward had mustered about 150.

On the 26th anniversary of the Battle of Bannockburn, Edward’s English
forces met Philip’s French forces at the Bay of Sluys in Flanders. The
French fleet was defending the bay, while Edward’s advanced towards
them. Philip had ensured that his ships were chained together, so as to
make an impenetrable barrier against the English forces.

However, after four hours of combat, the English ships broke through the
first line of French defense, and the French capitulated. Edward
captured all but 23 of the French ships, and estimates of between 16,000
and 18,000 French seamen and soldiers lost their lives. Sluys belongs on
the list of the greatest medieval battles because it was a turning point
in the Hundred Years War, and it solidified it in England’s favor.

8. The Battle of Agincourt, 25th October 1415

agincourt medieval battle illustration
The Battle of Agincourt, by Enguerrand de Monstrelet,15th century, via
the Paris Army Museum

Our next battle on this list is another from the Hundred Years War, but
this time towards the middle of the conflict. Under the Lancastrian
king, Henry V, English forces emerged victorious in not just one of the
greatest medieval battles of all time, but one of history’s greatest
underdog stories.

After a few decades of relative peace in the Hundred Years War, England
and France had resumed negotiations but they had turned sour. As a
result, England began to rearm and prepare for war – this time under
Edward III’s great-grandson, Henry V.

In the ensuing campaigns, English numbers had been decimated by disease,
and they tried to withdraw from English-held Calais but found their
route blocked by French forces at Agincourt. Despite their severe
numerical disadvantage — around 7,000 English soldiers to about 25,000
French — Henry V had no other option but to fight his way out.

The French forces were led by a nobleman called Charles d’Albret (King
Charles VI of France was severely mentally ill), while Henry V commanded
the English army. The English longbows, which had shown such prominence
in the early battles of the Hundred Years War under Edward III in
conflicts such as Crécy and Poitiers, once again proved their superiority.

The English forces routed the French and lost about 600 men, compared to
the 6,000 French who were killed, and the 2,000 who were captured and
mostly executed. The reason that Agincourt belongs on this list of the
greatest medieval battles is because it turned the Hundred Years War
back in the favor of England. It also proved that the longbow — despite
being used for almost a century — was still the superior weapon of the day.

9. The End of the Byzantine Empire: The Siege of Constantinople, 29th
May 1453

constantinople siege medieval battle illustration
The Last Siege of Constantinople, by Jean le Tavernier, c. 1455, via
Wikimedia Commons

This list of the greatest medieval battles would be incomplete without
including the tragic story of the fall of Constantinople, which signaled
the final collapse of the Roman Empire.

Sometimes referred to as the “Conquest of Istanbul” in Turkish, the Fall
of Constantinople was the culmination of a 53-day siege of the city,
which at the time was the capital of the Byzantine Empire. The
beginnings of the Byzantine Empire had been formed under Roman Emperor
Constantine I in 330, who established the capital, and it survived as
the Eastern Roman Empire after the collapse of the Western Roman Empire
in the sixth century.

Due to centuries of conflict between the eastern and western churches,
the Byzantines were effectively left on their own to defend their city
after they had predicted an assault from the Ottomans.

mehmed ii siege painting
Mehmed II, “the Conqueror”, by Gentile Bellini, 1480, via the Courtauld
Gallery

Unfortunately, this story is not one of underdogs. The Ottoman army,
commanded by the 21-year old Sultan Mehmed II (who became known as
Mehmed the Conqueror), numbered almost 200,000, while the Byzantines had
just over 10,000. It was always going to be an Ottoman victory.

Emperor Constantine XI Palaiologos led the Byzantine army which was
completely obliterated by Mehmed’s forces. Mehmed made Constantinople
the new capital of the Ottoman Empire after his victory, and not only
ended the Byzantine Empire but also the Roman Empire.

This is one of the most significant battles of all time, not just one of
the key medieval battles. It enabled the Ottomans to push further into
Europe, and they gained much more territory in the Balkans, which still
exhibits a Muslim influence to this day, particularly in countries such
as Bosnia and Herzegovina and Albania. Furthermore, it led to a change
in warfare — sieges had often been held up, with turrets firing huge
boulders at thick castle walls, but with the onset of gunpowder, castles
crumbled and changed military tactics forever.

Finally, the Fall of Constantinople is such a key event in medieval
history, that it is sometimes referred to as the end of the Middle Ages,
and the ushering in of the Early Modern period. However, some historians
disagree and instead prefer to turn to 1492, which is the final battle
on this list of the greatest medieval battles.

10. The Medieval Battle to Unify Spain: The Fall of Granada, 2nd January
1492

la rendicio grenada medieval battle painting
The Capitulation of Granada, by Francisco Pradilla y Ortiz, 1882, via
Cambridge University

The final battle on this list is another key event in medieval history,
and the whole year 1492 is often used to describe the change from the
Medieval Period to the Early Modern Period — particularly Columbus’
“discovery” of the Americas. However, the fall of Granada is just as
important to European history.

Muslims had ruled the Iberian Peninsula in various areas since the
conquest of Al-Andalus in 711. Thus, the fall of Granada — the Muslims’
last stand in Iberia — ended 781 years of Muslim rule in the Peninsula,
who were never to return again.

The Granada War had been going on since 1482 with various conflicts and
battles, but they all eventually culminated in the fall of Granada in
1492. The Granadan defenders were also plagued with internal conflicts,
while the Christian forces remained unified under the monarchs Ferdinand
II of Aragon and Isabella I of Castile, two monarchs who are some of
Spanish history’s most revered and respected rulers of all time: by
unifying their kingdoms, they defeated their mutual enemy.

alhambra palace photograph
The Alhambra Palace, Grenada, via the Alhamabra.org

Eventually, after realizing there was nowhere else to turn to, Muhammad
XII (also known as Boabdil) surrendered the magnificent Alhambra Palace
to the Christian forces who moved in. Allegedly, Boabdil’s mother was so
disappointed when he wept as he handed the keys to the Alhambra over
that she said: “You do well, my son, to cry like a woman for what you
couldn’t defend like a man.”

However, although Granada was now in Christian hands, that did not end
all conflict. If anything, it prevented the religious coexistence which
had survived for centuries. All of the Jews were forced to convert to
Christianity or face exile, and the same applied to the Muslims.

Even so, the fall of Granada is definitely one of history’s most
significant medieval battles, because of how it affected the Iberian
Peninsula to this day. Evidence of the Muslim influence is still very
much present in the wonderful Alhambra Palace today, but it is also
clear in Spain’s highly Catholic population that Islam has well and
truly left the Peninsula forever.

READ NEXT:
After The Fall Of Rome: Who Were The Barbarian Successor Kingdoms?

Author Image
By Chester Ollivier
BA (Hons) History
Chester is a contributing history writer, with a First Class Honours
degree BA (Hons) in History from Northumbria University. He is from the
North East of England, and an avid Middlesbrough FC supporter.

Read more by Chester Ollivier