The First Italian War, or Charles VIII's Italian War, was the opening phase of the Italian Wars. The war pitted Charles VIII of France, who had initial Milanese aid, against the Holy Roman Empire, Spain and an alliance of Italian powers led by Pope Alexander VI, known as the League of Venice.
25 January 1494: King Ferdinand I of Naples died and was succeeded by his son Alfonso II of Naples (who also laid claim to Milan). King Charles VIII of France disputed the succession, and began preparations for an invasion of Italy to enforce his claim on the Neapolitan kingship.
5–8 September 1494: Battle of Rapallo. A land battle involving the French fleet. French victory; Neapolitans abandoned Rapallo, which the French army sacked.
11 September 1494: French King Charles VIII and Louis of Orléans arrived in Asti and concluded an alliance with Duke Ludovico Sforza and Beatrice d'Este.
17 October 1494: skirmishes near Sant'Agata sul Santerno. Tactical Neapolitan victories.
19–21 October 1494: Sacking of Mordano. Franco–Milanese victory; the French soldiers sacked Mordano, the Milanese soldiers tried to protect the civilians.
26–29 October 1494: Siege of Fivizzano. French victory; the French army sacked the town.
8–9 November 1494: Florentine revolt against de' Medici. Florentine republican victory; Piero the Unfortunate (who had submitted to all the French demands) was ousted, the Republic of Florence restored under the de facto leadership of Girolamo Savonarola.
Mid-November – 28 November 1494: Tense French occupation of Florence. An anti-French revolt or a French sack of the city was averted, and Charles VIII marched on to Rome.
31 December 1494 – 6 January 1495: Peaceful French entry into Rome with Pope Alexander VI's permission, but some French looting took place.
? 1495: French conquest and destruction of the Castello di Monte San Giovanni Campano. French victory.
? 1495: French sack of Tuscania (Province of Viterbo). French victory.
22 February 1495: The French army captured Naples without a fight. Ferdinand II of Naples fled the city to Sicily, but kept fighting the French army elsewhere. Charles VIII was crowned king of Naples, and he appointed Gilbert, Count of Montpensier as his viceroy. Likely, the first documented outbreak of syphilis in history occurred amongst the French troops at Naples.
31 March 1495: Several Italian states (including Naples, Venice, Florence, Milan, the Papal States, Genoa and Mantua), Spain and the Holy Roman Empire formed the League of Venice to expel the French army from Italy. Milan defected from France to join the League of Venice.
2 May 1495: Battle of Rapallo (1495). League of Venice victory; the Genoese fleet defeated and captured the French fleet, and forced the French garrison of Rapallo to surrender. Much French war booty was lost, and Charles VIII's supply line was endangered.
30 May 1495: Charles split his army, leaving half of it behind to garrison the Kingdom of Naples, and taking the other half to march back to France.
11 June 1495: Occupation of Novara by Louis of Orléans.
28 June 1495: Battle of Seminara. French tactical victory; the French garrisons defeated the Neapolitan–Aragonese troops of Ferdinand II of Naples and Ferdinand II of Aragon (both Ferdinands were some of the last kings from the House of Trastámara).