Battle of Gainesville The Battle of Gainesville ( not to be confused with the First Skirmish of Gainesville of 14 February 1864 ) was fought on 17 August 1864 , when a Confederate force defeated Union detachments on a raid from the Union garrison in the Jacksonville , Florida , area . However , the other and first Battle of Gainesville was fought on 14 February 1864 , when a small unit associated with the February 1864 Florida Expedition , defeated a Confederate cavalry unit . Background . Gainesville , site of a railroad junction and depot in north central Florida , was the scene of two small - scale engagements during the war . On 14 February 1864 , the first battle occurred when about 50 Union troops entered the city intending to capture two trains . Company H of the 2nd Florida Cavalry with 130 men attempted to repulse this raid , but were defeated by the Union force , which successfully returned to Jacksonville after holding the town . Listed in the War ' s Official Orders is a General Order signed by Brigadier General Truman Seymour on 17 February 1864 , stating that he : " . . . especially desires to praise Capt . George E . Marshall , Co . G . 40th Mass . Mounted Volunteers , and his small command of forty - nine men who captured and held Gainesville for fifty - six hours , receiving and repulsing an attack from more than double his force , and , after fulfilling his mission successfully , returning to the designated place of rendevous . " Battle . The Battle of Gainesville took place on 17 August 1864 , in the town square ; many townspeople viewed the fighting from the windows of the nearby Beville house . A Union column of 342 men under the command of Col . Andrew L . Harris had occupied Gainesville that morning . It was composed of the 75th Ohio Mounted infantry , two companies of the 4th Massachusetts Cavalry , Battery A , 3rd Rhode Island Heavy Artillery with 3 cannon , and a small unit of Floridians loyal to the Union . They were attacked from the rear by soldiers of the Second Florida Cavalry under the command of Captain John Jackson Dickison ( companies H and F ) , supported by local militia , elements of 5th Florida Cavalry Battalion , and a small artillery battery of two cannons . Dickison ' s men numbered about 290 , although only 175 entered Gainesville and engaged in the fighting . The Union troops were tired from a two - day march from Baldwin in the August heat . They were taken by surprise and had not fully deployed when the Confederate attack began . After about two hours Col . Harris gave the order to retreat from Gainesville ; the Confederates continued to close in on the disorganized Union columns . Union losses numbered 28 dead , 5 wounded , 86 missing or unaccounted for , 188 captured , 260 horses and a 12 - pound howitzer ; the Confederate s lost three killed and five wounded , of whom two died the next day . About 40 Union troops , including Colonel Harris , escaped . He reported his column was destroyed by a large Confederate force of 600 — 800 men and three cannon . After hearing his account , the remaining Union forces in the north central Florida area withdrew to the garrisons at Jacksonville and St . Augustine . Gainesville remained in Confederate control for the duration of the war . External links . < br >