By January 1865, Owensboro, Kentucky saw its fair share of guerrilla activity. In September 1862, Adam Rankin "Stovepipe" Johnson's 10th Kentucky Partisan Rangers occupied the town for several hours (Johnson was absent from the regiment as he was travelling to Richmond), and that same morning, the partisans skirmished with the recruits of the 15th Kentucky Cavalry/38th Kentucky Mounted Infantry after their commander, Lieutenant Colonel Gabriel Netter, refused the demand of surrender of his camp. In the ensuing action, Netter was killed and the partisans fell back 10 miles south of town as hundreds of men from the Indiana Legion prepared to cross the Ohio River to reclaim the territory. The following day, the Indiana Legion made the only assault in their history as they attacked the Confederate troops at Sutherland's Hill and drove them from the area for good. Guerrilla activity continued on a small scale, usually small bands of thieves stealing horses and shooting at anyone that might get in the way.
In 1863 to early 1864, guerrilla and partisan activity was curbed somewhat by the presence of the newly formed 35th Kentucky Mounted Infantry. This regiment's sole purpose was to spread across the Green River region of western Kentucky and prevent guerrilla bands from forming, and to destroy those that already existed. This regiment performed its duties well, but was called to the eastern part of the state to participate in the failed attack on Saltville, Virginia. This movement of forces left Owensboro vulnerable to Confederate incursions.
Guerrilla activity outside town spiked again in 1864, as even more men took advantage of the chaos of war to carry out lawless deeds. One Kentucky county not far away was reportedly "infested with guerrillas," and that "Horses, guns, and eatables had better watch out," commented the Owensboro Monitor. United States Colored Troops garrisoned the town for a time, capturing a few guerrilla bands in the surrounding countryside in the process. As Randy Mills notes, attacks upon black troops in Owensboro were rarely successful due to the sheer number of USCT troops present, the additional white regiments, and the occasional gunboat on the Ohio River. In August, guerrilla Jake Bennett and his band of twenty swiftly rode into Owensboro and demanded money from the bank. After threatening to burn the courthouse over the lack of money, Bennett's attention was given to the wharfboat just returned from Louisville, guarded by one officer and nine USCT troops. The rest of their regiment, the 108th US Colored Infantry, recently departed just a few days before along with the two armed steamboats. Bennett's men surprised the troops on the boat, killed Lieutenant Walters, and set fire to the vessel. Two of the black soldiers were shot and thrown overboard, while another's charred body was found once the flames were extinguished. Three of the men escaped up the river bank, and three more were rescued from the hull by the town's citizens. After his men stole some articles from a jewelry store, robbed some citizens, and burned whatever government supplies they could find, the guerrillas departed. Bennett's actions were condemned by all political persuasions in Owensboro. 
In December 1864, Major Walker Taylor, nephew of President Zachary Taylor, arrived on the outskirts of Owensboro were a hot fire was exchanged with the Federal pickets for much of the afternoon, with neither side suffering much in the way of casualties. Taylor rode into Owensboro under flag of truce later that night and demanded the town's surrender. Naturally, the demand was refused, and instead of renewing the attack, Taylor spent the "most of the night sociably with the Federal officers in the court-house." Another source mentions that Taylor and the Union officers drank, played cards, and socialized with it being just a couple nights before Christmas. Interestingly enough, Taylor's Confederate presence had prevented the more violent guerrillas from operating wherever he and his troops happened to be.
One such rash, and extremely violent, guerrilla was William H. Davison, a former Union captain in the 17th Kentucky Infantry. In 1862, Davison resigned his commission due to the Emancipation Proclamation, and had since turned to full out blood thirsty guerrilla, only slightly aligned with the rebel cause. Davison and his "Hyenas" terrorized western Kentucky for months with murders, thieving, and executions. Just weeks after Major Taylor's cordial visit to Owensboro, Davison arrived with a less pleasant attitude. 
In January 1865, Davison entered Owensboro, which again was empty of any Union troops. Davison demanded $400, which only a portion was raised. Davison allowed his men to rob more than $2,000 in goods from stores and citizens before performing his final act. Incensed that the Daviess County courthouse formerly housed black Union soldiers, Davison ordered the building destroyed. In a matter of minutes, flames engulfed the six year old building, sending ash and burning papers into the sky. A new courthouse was not erected until 1868 
After the news of the burning reached Union authorities in Evansville, the decision was made to no longer tolerate any such guerrilla activity in a city the size of Owensboro. On January 11, a detachment of the veteran 27th Kentucky Infantry, Colonel John. H. Ward in command, embarked upon the Grey Eagle for Owensboro from Brandenburg. When the steamboat arrived at the landing, some of the remaining guerrillas made their way toward the steamer, intending to take and pillage it. The Kentucky soldiers, veterans since 1862, concealed themselves to make the boat appear defenseless. Some of the guerrillas boarded the vessel to speak with the captain, while many more watched from the shore. A signal was given, and the Federal troops "commenced operations." They rushed forth, firing upon the guerrillas as they scattered throughout the town, or "skedaddled" as reported by the Evansville Daily Journal, but not before several of them were struck by Union rifles. The soldiers fanned out through the town, searching homes, buildings, and businesses for the hated guerrillas. Several were killed, wounded, and captured by the Federal soldiers, without the loss of a single Union man. These men that "held" Owensboro were probably part of Davison's band, and the return of Union order safeguarded Owensboro for the rest of the war and commenced the return of shipping along the Ohio.
The 27th Kentucky remained for about a month, patrolling into the heart of the county and capturing many more supposed guerrillas. Many of the captured were teenagers, with many of these "boys...persuaded to leave home and join these lawless bands." The guerrillas, for some unexplained reason, mistook several patrols by the 27th as fellow bushwhackers and frequently rode up to them, only to discover their mistake when it was too late. Ward pushed his superiors for discretion when dealing with such men. Ward asked, "Shall I execute such men, or send them to Louisville with charges? I would suggest that those coming in and surrendering themselves voluntarily to be left somewhat to my discretion." He continued to emphasize that many of these so-called guerrillas "would be glad to surrender themselves to the authorities if assured of lenient treatment."
In March, the 27th's commanding officer, Colonel Ward, was placed in command of the Western Division of the Second Military District of Kentucky, with his headquarters at "Owensborough." While there, the regiment "won a fine name for discipline and order even from the most decided rebels, and it was probably as well disciplined as any volunteer regiment in the Union army." With the presence of such experienced and disciplined troops, Daviess County was pacified from any significant guerrilla violence. The Owensboro Monitor commended Ward and the 27th as "a model regiment--and in this expression officers and men, from Colonel down, are included. They carried with them the good will of the people, and they are remembered and spoken of with great respect by our people. The reign of Col. Ward and his regiment did more to soften the hostility of the people to military reign, and make loyal citizens of the disloyal, than would a thousand years of rigorous rule." In February, the 27th was ordered elsewhere, many of the soldiers nearing the end of their terms. It was replaced by the 18th and 12th Kentucky Cavalry regiments, and later the 185th Ohio Infantry. By May 1865, peace finally returned to the Owensboro region.
 Owensboro Monitor, July 6, 1864, 2.; August 31, 1864, 2.; Randy Mills, "Confederate Raider...Criminal...Hero: Jake Bennett's Civil War," Journal of the Indiana Academy of the Social Sciences (2012) Vol. 15, Issue 1, 46.
 History of Daviess County, Kentucky, 175.; J.B. Nation, Major Walker Taylor, CSA, 10.
 Stuart Sanders, "The Radicalization of 'Bloody-Handed' Bill Davison: How a Union Soldier Became a Pro-Confederate Bushwhacker," The Register of the Kentucky Historical Society (2018) Vol. 16, no. 2, 201.
 Evansville Daily Journal, January 12, 1865, 2.; History of Daviess County, 176-177.;
 History of Daviess County, 176-177.; The War of the Rebellion: A Compilation of the Official Records of the Union and Confederate Armies, Series 1, Vol. 49, 589-590.
 OR 49, pt. 1, 874.; Thomas Speed, The Union Regiments of Kentucky (Louisville, Kentucky: Courier-Journal Printing Company, 1897), 559.; History of Daviess County, 177.; Owensboro Monitor, May 31, 1865, 2.