Captain John J. Dickison had enjoyed a string of successes in defending Florida from Union troops.  Along with his own command of Company H, 2nd Florida Cavalry and various units occasionally serving with him, he seldom mustered a force of more than 200 soldiers.  Yet time and again, Dickison repeatedly thwarted Union efforts in the state.  In August of 1864, Dickison would face his largest engagement of the war.
   On August 15, 1864, Union troops marched from Baldwin in two columns.  One force consisted of three U.S. Colored infantry regiments and the 3rd Rhode Island Artillery with three cannons.  The other column commanded by Colonel Andrew Harris of the 75th Ohio Mounted Infantry, included the 75th Ohio Mounted Infantry and one cannon of the 3rd Rhode Island Artillery.  The two columns took different routes, and met that night at a place called Trail Ridge.   Here Colonel Harris added to his command some of the 75th Ohio that had been with the infantry column.  Colonel Harris' column  resumed their march the same night, and early in the morning of August 16 the cavalry force was at the town of Starke.  Here about 100 soldiers joined the command, including two companies of the 4th Massachusetts Cavalry commanded by Captain Joseph Morton and a small force of Floridians loyal to the Union. Now the cavalry column numbered some 342 troops.
   Captain Dickison was at Waldo, 14 miles south of Starke, on August 16 when he received word of the Union troops at Starke.  He assembled a force that included his own Company H, 2nd Florida Cavalry with 130 men, Captain Samuel Rou's Company F, 2nd Florida Cavalry, a detachment of Company H, 5th Florida Cavalry Battalion, ninety new infantry troops, and an artillery battery with two cannons commanded by Lieutenant A. J. Bruton.  The Union cavalry column left Starke at about 7:30 on the morning of August 16.   The infantry to be commanded by Colonel Elias Earle, one of Governor Milton's staff officers, marched toward Gainesville, while Dickison pursued the enemy with the cavalry and artillery.  A small force of local militia joined the command, and now Dickison had some 290 soldiers.
   Colonel Harris' troops made their way through the countryside, raiding plantations as they went. Around 6:30 on the morning of August 17, the Union cavalry arrived at the town of Gainesville, 12 miles from Waldo.  Seventy local militia commanded by Judge Thomas King awaited the Federals, but they were driven from the town by Company B, 4th Massachusetts Cavalry.  Colonel Harris deployed his men about the town and posted pickets.  The marches had taken their toll, and the horses were much in need of a respite. The men were ordered  to leave with  their accoutrements on  but also to attend to their mounts while coffee was made for the troops.  Once they were posted in a grove of trees and had seen to their horses, the artillery troops wandered the town. Scarcely had they returned to their battery when an artillery round struck near their position.
    Captain Dickison had halted his march some two miles from Gainesville when he saw the rear guard of the Federals.  When they had entered the town,  the Confederates advanced to within a mile of Gainesville where they encountered Union pickets and formed into a line of battle while the artillery open fire.  At about 7:00 A.M., Union pickets south of town reported the approach of the Southerners. Colonel Harris promptly began to organize a defense.  The 75th Ohio about-faced, the right flank becoming the left and their left was now the right flank.  Both flanks were anchored on swamps and brush, and Union troops took up positions along the railroad and in the depot.  Only one company of the 75th Ohio remained mounted, and was posted near a railroad fill and surrounding fences.  The 4th Massachusetts Cavalry was  in reserve, and the 12-pound howitzer of the 3rd Rhode Island Artillery was placed along the road near the center of the Union line.
   Colonel Harris' troops were not fully deployed when the Confederate attack began.   With their artillery engaged, most of the Confederates dismounted and advanced, driving in the Union pickets.  The railroad depot on the Confederate left was attacked by Captain Rou's and Lieutenant McCardell's troops.  The 5th Florida Cavalry Battalion under Lieutenant A. J. Dozier was to push  the enemy from the road in the Union center while a mounted company commanded by Lieutenant McEaddy moved on  the  Southern right. 
   For nearly two hours the battle would rage in Gainesville.  The Union line held the initial attack, but despite the Federals' superior numbers, the Confederates began to encircle the town.  Union troops were pushed from the railroad depot and the Southern troops opened a crossfire on the artillery limber..  Of the six horses on the limber, five were killed along with the artilleryman holding them.  Nevertheless, the Rhode Island battery kept up a steady fire from its position near the Beville Hotel, and soon found the range of the Southern artillery.  Lieutenant Bruton moved his guns and soon renewed the duel.

   The Union troops put up a steady fight.  The 4th Massachusetts Cavalry had been deployed into the battle, helping to briefly hold back the Confederates. The flanks of the 75th Ohio had been extended and for a time the Union line held.  But by 9:00 A.M. Colonel Harris realized his situation.  The enemy was surrounding him, his troops had been pushed back, many of the horses had been hit, and his artillery had nearly expended its ammunition.  Harris then ordered a retreat from the town.
   The Federals had held for nearly two hours, but now the line began to break as they retreated from the town.  With the Confederates closing in as they left their line, the Union troops had no time to make an organized retreat,  and Federal columns attempted to withdraw from the town in several directions.  Union Captain Morton, along with some of the cavalry and the howitzer, mistakenly took the wrong road.  Colonel Harris caught up with him and led the troops to the road to Waldo, but the gun was halted when one of the horses was hit. The Confederates closed in and captured the cannon and many of the artillery troops.  Captain Dickison rode through the town, ordering his troops to their mounts to pursue the enemy, and many of the Federals were captured as they attempted to withdraw.  Lieutenant Colonel Benjamin Morgan of the 75th Ohio and the advance troops were driven from the Waldo Road.  Morgan had to abandon his wounded horse and went on foot through the swamps before being captured. Some 40 Union soldiers, Colonel Harris among them, escaped to safety.
   Of the Confederate force, 175 took part in the battle.  The rest did not enter the town until following the engagement and assisted in pursuing the enemy.  Southern troops searched the countryside and for a few days, some of the scattered Union soldiers were captured while other Federals found their way to Union forces. The Union losses were high: 28 dead, 5 wounded, and 188 captured.  The Confederates also captured 260 horses and the 12-pound howitzer.  Southern casualties were three killed and five wounded; two of these men were mortally wounded and died the following day.  Colonel Harris' report of the battle put the number of Confederate troops at 600 to 800, with three pieces of artillery.
   .  Upon hearing of the battle and the loss of the cavalry column, the Union infantry column was withdrawn to a Federal garrison. 
   The Battle of Gainesville was for a time an annual re-enactment held in the town of Orange Springs in Marion County.