42 BC

Liberators' civil war: Mark Antony and Octavian decisively defeat an army under Brutus in the second part of the Battle of Philippi, with Brutus committing suicide and ending the civil war.

Mark Antony and Octavian defeat Brutus’s forces at Philippi, leading to Brutus’s suicide and the end of the Liberators’ civil war.
After Julius Caesar’s assassination, the Liberators’ civil war continued as the Second Triumvirate pursued the conspirators. On October 23, 42 BC, Mark Antony and Octavian engaged Brutus’s army in the second showdown at Philippi in Macedonia. The triumviral forces trapped and overwhelmed the attackers, forcing Brutus to withdraw. Facing defeat, Brutus chose suicide over capture. This victory secured Antony and Octavian’s grip on Roman power and paved the way for the transformation from Republic to Empire.
42 BC Liberators' civil war Mark Antony Octavian Brutus Battle of Philippi
1086day.year

Spanish Reconquista: At the Battle of Sagrajas, the Almoravids defeats the Castilians, but are unable to take advantage of their victory.

Almoravid forces defeat the Castilian army at the Battle of Sagrajas, stalling the Christian Reconquista in Iberia.
On October 23, 1086, the Almoravid dynasty from North Africa clashed with Alfonso VI of Castile’s forces at Sagrajas (also called Zalaca) near Badajoz. The Berber cavalry’s superior tactics routed the Castilian knights, inflicting heavy casualties and capturing banners. Despite this victory, logistical challenges and shifting Muslim alliances prevented the Almoravids from exploiting their success to recapture Toledo. The battle demonstrated the continuing strength of Islamic states in Iberia and forced Christian kingdoms to seek new alliances. It marked a temporary check on the Reconquista, which would resume over the following centuries.
1086 Spanish Reconquista Battle of Sagrajas Almoravids Castilians
1157day.year

The Battle of Grathe Heath ends the Danish Civil War.

Royalist forces defeat the supporters of rival claimants at the Battle of Grathe Heath, ending Denmark’s civil war.
The Battle of Grathe Heath on October 23, 1157, was the decisive engagement in the Danish Civil War between factions backing King Sweyn III, Duke Canute V, and Prince Valdemar. Forces loyal to Valdemar I confronted Sweyn’s army on the heath near Aarhus. Sweyn was killed during or after the battle, and Canute had earlier withdrawn, leaving Valdemar as sole ruler. His victory ended years of dynastic strife and began a period of consolidation and reform known as the Valdemar era. Grathe Heath’s outcome shaped medieval Denmark’s centralized monarchy and law codes.
1157 Battle of Grathe Heath Danish Civil War
1641day.year

Irish Catholic gentry from Ulster attempt to seize control of Dublin Castle, the seat of English rule in Ireland, so as to force concessions.

Ulster’s Irish Catholic gentry attempt to seize Dublin Castle in a bold bid to force English concessions.
On October 23, 1641, a group of Ulster’s Catholic gentry plotted to capture Dublin Castle, the administrative heart of English rule in Ireland. They aimed to secure key military and political leverage to negotiate relief from anti-Catholic legislation. Although they gained initial access to some city gates, loyal forces inside Dublin thwarted the coup. The failed attempt escalated tensions and heralded the wider Irish Rebellion of 1641. It set the stage for the Confederate Wars that would engulf Ireland for the next decade.
1641 Irish Catholic Ulster seize control Dublin Castle English rule in Ireland
1642day.year

The Battle of Edgehill is the first major battle of the English Civil War.

Royalist and Parliamentarian armies meet at Edgehill in the first major battle of the English Civil War.
The Battle of Edgehill on October 23, 1642, marked the opening large-scale conflict between King Charles I and Parliament’s forces. Located in Warwickshire, the encounter saw roughly equal numbers on both sides engage in inconclusive fighting. Cavalry charges, infantry volleys, and the inexperienced pikemen tested the mettle of both armies. Although the Royalists claimed a slight tactical advantage, neither side secured a decisive victory. Edgehill demonstrated the war’s brutal new style and foreshadowed years of civil strife across Britain.
1642 Battle of Edgehill English Civil War
1798day.year

The forces of Ali Pasha of Janina defeat the French and capture the town of Preveza in the Battle of Nicopolis.

Ali Pasha's troops rout French forces and seize Preveza during the Battle of Nicopolis.
Amid the turbulence of the French Revolutionary Wars, Ali Pasha of Janina engaged remaining French garrisons in northwestern Greece. On October 23, 1798, his forces confronted a French detachment at Nicopolis near the town of Preveza. Utilizing superior knowledge of the local terrain, Ali Pasha secured a decisive victory, overrunning French defenses and capturing Preveza. The triumph effectively ended French ambitions in the region and reinforced Ali Pasha's authority over Epirus. This engagement further solidified his status as a dominant regional power under the Ottoman Empire. The Battle of Nicopolis demonstrated the interplay of local and European powers during the late 18th century.
1798 Ali Pasha of Janina French Preveza Battle of Nicopolis
1856day.year

Second Opium War: Dissatisfied with imperial commissioner Ye Mingchen's reparations for the alleged slighting of a British-owned vessel and at Consul Harry Parkes's urging, British Rear-Admiral Michael Seymour launches an assault on the Barrier Forts outside Canton in the first military engagement of the Second Opium War.

British forces under Rear-Admiral Michael Seymour launch the first assault of the Second Opium War on Canton’s Barrier Forts.
On October 23, 1856, British Rear-Admiral Michael Seymour ordered an assault on the Barrier Forts guarding the Pearl River near Canton (Guangzhou). The attack was prompted by grievances over Commissioner Ye Mingchen’s handling of reparations for the alleged insult to a British vessel. Supported by ships including HMS Furious, British marines and sailors stormed the forts under heavy fire. This engagement marked the outbreak of the Second Opium War between Britain and Qing China. The fortifications fell within hours, demonstrating British naval superiority. The clash escalated hostilities and set the stage for subsequent campaigns forcing China to concede to Western demands.
1856 Second Opium War Ye Mingchen Harry Parkes's British Michael Seymour an assault on the Barrier Forts outside Canton Second Opium War
1864day.year

American Civil War: The Battle of Westport is the last significant engagement west of the Mississippi River, ending in a Union victory.

The Battle of Westport, the final major Civil War engagement west of the Mississippi, ends in a Union victory.
In October 1864, Confederate Major General Sterling Price led a raid into Missouri aiming to capture Union-held territory and influence the upcoming US elections. On October 23, the armies clashed near Westport, on the outskirts of Kansas City. Union forces under Major General Samuel R. Curtis repelled repeated Confederate assaults across brushy terrain. Intense fighting ensued, with both sides suffering significant casualties. By evening, Price’s troops were forced to retreat southward, abandoning hopes of seizing St. Louis. The Union victory at Westport effectively ended Confederate operations west of the Mississippi River. Historians often refer to this engagement as the 'Gettysburg of the West' given its scale and impact.
1864 American Civil War Battle of Westport Mississippi River Union
1911day.year

The Italo-Turkish War sees the first use of an airplane in combat when an Italian pilot makes a reconnaissance flight.

An Italian pilot conducts the first military reconnaissance flight in history during the Italo-Turkish War.
On October 23, 1911, during the Italo-Turkish War, an Italian Army aviator undertook the first military reconnaissance flight in combat history over the Libyan desert. Flying in a fragile monoplane, the pilot traced Ottoman troop positions and fortifications, using a camera to record images from the air. This mission demonstrated the reconnaissance potential of aircraft, providing commanders with unprecedented battlefield information. The flight marked the beginning of aerial intelligence gathering and foreshadowed the use of airplanes for artillery spotting and bombing. Although the aircraft remained unarmed, its successful operation under combat conditions captured the attention of militaries worldwide. The Italian innovation reshaped military strategy and heralded the dawn of modern air warfare. Subsequent missions would expand the airplane’s role into direct combat and logistics support.
1911 Italo-Turkish War
1912day.year

First Balkan War: The Battle of Kumanovo between the Serbian and Ottoman armies begins.

The Battle of Kumanovo begins as Serbian and Ottoman forces clash in the First Balkan War.
On October 23, 1912, Serbian and Ottoman armies engaged in the Battle of Kumanovo, one of the opening major clashes of the First Balkan War. The Serbian Third Army, commanded by Crown Prince Alexander and General Božidar Janković, advanced from the north toward Ottoman positions near Kumanovo. Ottoman forces of the Vardar Army, led by Mahmud Muhtar Pasha, resisted fiercely along mountainous terrain. Intense infantry and artillery exchanges lasted throughout the day, with both sides suffering significant casualties. By nightfall, Serbian troops had broken the Ottoman lines, forcing a retreat toward Skopje. The victory secured northern Macedonia for Serbia and undermined Ottoman control in the Balkans. The battle’s outcome was a pivotal moment that accelerated the collapse of Ottoman rule in southeastern Europe.
1912 First Balkan War Battle of Kumanovo
1923day.year

German October: Due to a miscommunication with the party leadership, a militant section of the Communist Party of Germany launches an insurrection in Hamburg.

A faction of the German Communist Party launched an armed insurrection in Hamburg, aiming to spark a socialist revolution.
German October was a brief uprising in Hamburg in October 1923, where a local militant faction of the Communist Party of Germany (KPD) attempted to seize power. The action was spurred by a miscommunication that led militants to believe the national party leadership supported an armed revolt. Over several days, insurgents occupied public buildings and clashed with police, causing significant unrest in the city. However, without broader party backing or coordination, the revolt was swiftly suppressed by government forces. Many participants were arrested, and the insurrection deepened divisions within the KPD. The failed uprising underscored the fragile state of post-World War I Germany and the volatility of communist movements. Despite its short duration, the German October influenced future revolutionary tactics and the party's internal dynamics.
1923 German October Communist Party of Germany an insurrection in Hamburg
1924day.year

Second Zhili–Fengtian War: Warlord Feng Yuxiang, with the covert support of the Empire of Japan, stages a coup in Beijing against his erstwhile superiors in the Zhili clique, crippling their nearly victorious war effort against the Fengtian clique and forcing them to withdraw from northern China.

During the Second Zhili–Fengtian War, warlord Feng Yuxiang, covertly supported by Japan, staged a surprise coup in Beijing that crippled the Zhili clique's war effort.
In October 1924, amid the Second Zhili–Fengtian War for control of northern China, General Feng Yuxiang turned against his Zhili-aligned allies. With covert backing from the Empire of Japan seeking greater influence over Chinese affairs, Feng led his troops in a swift operation to seize Beijing. They detained senior Zhili commanders and took control of government buildings, catching the Zhili clique off guard. The coup undermined the Zhili forces, who had been close to victory over Zhang Zuolin's Fengtian faction. Deprived of their capital's support, Zhili troops retreated from the front lines, effectively ending their campaign. Feng proclaimed a new military government and attempted to negotiate a settlement, though lasting peace remained out of reach. The event exposed the extent of Japanese interference in the Chinese warlord era and accelerated the decline of the Zhili clique. It would shape the power dynamics that eventually led to Chiang Kai-shek's Nationalists consolidating control.
1924 Second Zhili–Fengtian War Feng Yuxiang Empire of Japan stages a coup in Beijing Zhili clique Fengtian clique