Following his graduation from West Point, he was commissioned a Second lieutenant, Third Artillery in June 1857 and became part of the expedition under General Wright against the northern Indians. During this campaign, he reportedly distinguished himself in the Battle of Four Lakes and Spokane Plains and acted as Adjutant of the Artillery Battalion. In 1859, Kip published an account of the campaign in a book entitled Army Life on the Pacific. In 1861, at the beginning of the U.S. Civil War, he was Adjutant of the Third Artillery. Shortly thereafter, he resigned to join the staff of General Edwin Vose Sumner's as senior aide-de-camp, achieving the rank of Major. He was a part of the Army of the Potomac which saw action in the Battles of Yorktown, Williamsburg, Fair Oaks, Seven Pines, Savage's Station, Glendale, Malvern Hill, Antietam, Fredericksburg, and Mine Run which lasted from November 1863 until December 1863. From June 25 to July 1, 1862 during the Seven Days Battles, he was acting Adjutant General of General Sumner's Corps. Following the battles, Sumner recommended him for brevet Captain and brevet Major to the War Department for gallantry, however, the Senate failed to act on any recommendations from General George B. McClellan's campaign. After the death of General Sumner in March 1863, Kip went to work on the staff of General John E. Wool and was assigned to the Headquarters of the Department of the East, as Assistant Inspector General of the Artillery. Six months later, he again joined the Army of the Potomac and was assigned to the staff of Brevet Major General Robert O. Tyler, as Inspector of the Artillery Reserve, taking part in the Battle of Rappahanock Station. He was later appointed aide-de-camp on the staff of Major General Philip Sheridan where he fought in the Battles of Trevilian Station in 1864, where he was wounded, Cedar Creek, where he was slightly wounded again in 1864. On June 11, 1864, he was brevetted Captain "for gallant and meritorious service at the battle of Trevillian Station, Va." In 1865, he was part of the Battles of Dinwiddie Court House, Five Forks, High Bridge, Sailor's Creek, Appomattox Station, and Appomattox Court House, where Confederate General Robert E. Lee surrendered. On March 31 1865, he was brevetted Major "for gallant and meritorious service in the Cavalry campaign from Winchester to Petersburg and at the battle of Dinwiddie Court House, Va." and on April 1, 1865, he was brevetted Lieutenant Colonel "for gallant and meritorious service at the battle of Five Forks, Va." Kip resigned from the Military in 1867.
Lorillard Kip, who died unmarried of typhoid fever, aged 25.
Kip died on November 17, 1899 at his residence, 452 Fifth Avenue, in New York City after having been ill for nearly three weeks from "stomach trouble." His funeral was held Grace Church in New York and he was buried at Green-Wood Cemetery in Brooklyn, New York. In The New York Times write up of his funeral, it stated "There were society men, old and young; horsemen of more or less prominence, and roadhouse keepers. The number of women present was not especially large." After his death, his widow sold their Fifth Avenue home, took a camp in the Adirondaks, and died in poor health in 1903.
Descendants
Through his daughter Edith, he was the grandfather of four, including Lawrence B. McCreery and Lorillard Kip McCreery from her first marriage, and Victor Henry Coventry, named after Henry's brother-in-law, Prince Victor Duleep Singh, and Cecil George Coventry, who died young, from her second marriage.