Battle of Manila ( 1899 ) The Battle of Manila , the first and largest battle fought during the Philippine – American War , was fought on February 4 and 5 , 1899 , between 12 , 000 Americans and 15 , 000 Filipinos . Armed conflict broke out when American troops , under orders to turn away insurgents from their encampment , fired upon an encroaching group of Filipinos . Philippine President Emilio Aguinaldo attempted to broker a ceasefire , but American General Elwell Stephen Otis rejected it and fighting escalated the next day . It ended in American victory , although minor skirmishes continued on for several days afterward . Disposition of forces . Filipino forces . After the First Battle of Manila and the surrender of the city to American forces by the Spanish , General Aguinaldo demanded occupation of a line of blockhouse s on the Zapote Line , which had been the Spanish defensive perimeter . General Otis initially refused this , but later said that he would not object unless overruled by higher authority . There were about between 20 , 000 to 50 , 000 Filipino troops surrounding Manila ; their distribution and exact composition are only partially known . American forces . U . S . Army forces numbered some 800 officers and 20 , 000 enlisted men . Of these , some 8 , 000 were deployed in Manila and 11 , 000 in a defensive line inside the Zapote line . The remaining American troops were in Cavite or in transports off Iloilo . First shots . Sources generally agree that the first shots were fired by Private William Walter Grayson , a British citizen who had immigrated to America c . 1890 , had enlisted as a volunteer soldier in Lincoln , Nebraska , in May 1898 , a month after the Spanish - American War erupted , and had deployed with his unit to the Philippines in June 1898 . Grayson ' s unit , the First Nebraska Volunteer Infantry under Colonel John M . Stotsenburg , had been encamped in Santa Mesa , Manila , since December 5 , 1898 . During the time of their encampment , there had been incidents on and around the San Juan Bridge , located just to the east of their encampment area . On the morning of February 4 , Stotsenburg ordered , " Your orders are to hold the village . If any armed men come into our lines order them out . If they persist in coming , summon enough men to arrest them . In case an advance in force is made , fall back to the pipeline outpost and resist occupation of the village by all means in your power , calling on these headquarters for assistance . " In a report later that day , Lt . Burt D . Wheedon , wrote , " On the morning of February 4 the insurgents ordered our men to move out of town ( Santol ) , and upon their refusal to do so the former said that they would bring a body of men and drive them back when night came . " Lt . Wheedon took charge of an outpost on Santol road at seven in the evening and , at 7 : 30 , orders were given saying , " No armed insurgents to enter the town or vicinity . . . Halt all armed persons who attempted to advance from the direction of the insurgents ' lines which lie between blockhouses 6 and 7 and the San Juan Bridge and order them back to their lines . if they refused to go , to arrest them if possible , or if this was impossible , to fire upon them . . . Patrol each of the roads leading to Blockhouses 6 and 7 for 100 yards every half hour . " ( Blockhouse 6 was located on the city line just southeast of what is now Santol Street . Blockhouse 7 was about north - northeast of a point where the water pipe crossed Santol road ) . At about 8 pm on February 4 , 1899 , Grayson , along with Private Orville Miller and one other man advanced from Santol towards Blockhouse 7 , suddenly encountering four armed men after about five minutes of patrolling . According to Grayson ' s account , he and Miller called " Halt ! " and , when the four men responded by cocking their rifles , they fired at them and retreated to Santol . Personal accounts by Grayson claim that he " dropped " two and Miller one , but neither American nor Filipino official reports mention anyone being hit . Some sources assert that the encounter took place on San Juan Bridge . A marker which had stood on that site was ordered moved to Santa Mesa in 2003 after studies by Dr . Benito Legarda , formerly chair of the National Historical Commission of the Philippines concluded that the shot was fired somewhere between Blockhouse 7 ( within Manila ’ s boundary ) and Barrio Santol ( Sampaloc District ) on the connecting road that is now Sosiego . Reactions of Aguinaldo and Otis . Aguinaldo was away in Malolos when the conflict started on the 4th . That same night , a Filipino captain in Manila wired him in Malolos , stating that the Americans had started the hostilities . Aguinaldo wanted to avoid open conflict with the Americans while maintaining his position of leadership with his nationalist followers . The next day ( February 5 ) Aguinaldo sent an emissary to General Otis to mediate , saying " the firing on our side the night before had been against my order . " Otis , who was then confident that a military campaign against Aguinaldo would be swift , was a veteran of the American Indian Wars and reacted much as he might have to his Sioux opponents decades before : " Fighting having begun , must go on to the grim end . " Aguinaldo then reassured his followers with a pledge to fight if forced by the Americans , whom he had come to fear as new oppressors come to replace the Spanish . Battle . Caught off guard by the sudden outburst , the Filipinos remained in their trenches and exchanged fire with the Americans . A Filipino battalion mounted a charge against the 3rd U . S . Artillery , routed a company of American soldiers , and succeeded in capturing two artillery pieces for a little while . The Filipino troops had been caught unprepared and leaderless , as their generals had gone home to their families for the weekend . The American soldiers , in contrast , were ready and needed only to follow previously prepared planning . The next day , Brigadier General Arthur MacArthur ordered an American advance . When Filipino officers did arrive on the field , many influential leaders tried to stop the fighting . Aguinaldo sent emissaries to negotiate a cease fire . But both Otis and MacArthur thought the crisis should be brought to a head and refused to negotiate . General MacArthur , in command of the North of Manila , had developed a defensive plan which called for his entire division to launch an all - out offensive along the Santa Mesa Ridge in the event of attack , capture the blockhouses , and seize the Chinese hospital and La Loma Cemetery . General Anderson , along the southern lines , believed he faced imminent attack . With permission from Otis , he sent his entire division in a preemptive strike at first light . The battle of February 5 was fought along a 16 mile front and was the biggest and bloodiest of the war . It involved all or part of 16 American regiments and thousands of Filipinos . American casualties totaled 238 , of whom 44 were killed in action or died from wounds . The U . S . Army ' s official report listed Filipino casualties as 4 , 000 , of whom 700 were killed , but this is guesswork . The Filipinos were shocked when the Americans attacked . They were used to Spanish tactics of retreating into fortified cities after a night time raid . MacArthur ' s attack in the north captured the ridge overlooking Manila . ( MacArthur was later promoted to Major General and became Governor - General of the Philippines . ) After initial confusion , Brigadier General Thomas M . Anderson ' s attack in the south captured the village of Pasay and Filipino supplies stored there . The Filipinos were counting on an uprising by the citizens of Manila to divide American forces and interrupt American supply lines . Although some fires were set inside the city , no general uprising occurred . However , some small units of Philippine soldiers who had not been part of the force that was routed , skirmished with the Americans for several days on the outskirts of Manila before being driven out . Aftermath . While both sides suffered losses , the Filipinos suffered far greater casualties . The Americans lost 50 to 60 killed and more than 200 wounded . The Filipinos suffered the loss of roughly 2 , 000 killed , wounded , or captured . The high casualty figures are due largely to the Americans use of artillery , warships and firearms . Order of battle . U . S . . VIII Corps – Major General Elwell S . Otis