The 1st Georgia was placed on the right. Steele’s Battalion held the center, and the 2nd Tennessee was placed upon the left. Huwald’s Battery was placed in advantageous positions.
General Gillmore began his attack at 12:30 p. m., with an artillery barrage, which was damaging to the Confederate defenses. Meanwhile he placed the 1st Kentucky dismounted in the woods to the right. The 7th Ohio and the four Rodman guns were placed in the center. Dismounting, the 44th & 45th Ohio took a position on the left. Believing his mountain howitzers to be useless, Gillmore, placed them in reserve.
General Pegram’s and Colonel Scott’s after action reports differ as to how events unfolded during the three-hour battle to hold the hill. Colonel Scott took the 1st Louisiana and 1st Tennessee and attempted to flank the position of the 1st Kentucky Cavalry, so that they could get to the rear of the Union artillery. Pegram claims he held out for an hour awaiting Scott’s attack, which he felt should have taken only 10 minutes to have begun. Colonel Scott stated that an aide to General Pegram, Lt. J. F. Ranson, had countermanded the order and had halted the bulk of his command without his knowledge. As a result Scott charged the Union position with 30 troopers managing to capture just three horses. Furious, Scott retired and confronted Lt. Ranson, chastising him for delivering the order to halt to Lt. Colonel Nixon instead of himself, and cursing General Pegram in the process. In the meantime General Pegram reversed himself and ordered the flanking attack once again.
Observing the Confederate maneuvering, General Gillmore took steps to prevent its success. As Colonel Scott withdrew his troopers for a second attempt, Gillmore ordered the 44th and 45th Ohio Infantry and the 7th Ohio Cavalry to storm the hill, which they captured after a desperate defense of a thicket by three companies of the 2nd Tennessee. Captain Footman of the 1st Florida Cavalry had sent a detachment to support Pegram but they arrived too late to be of assistance. Gillmore quickly sent the 7th Ohio to support the 1st Kentucky by flanking Scott’s position, while parts of the 44th and 45th Ohio Infantry marched to the support as well.
After regrouping his command of approximately 330 men, Colonel Scott split them into three groups. Lt. Colonel Nixon with 6 companies and Captain Mathews with 4 companies of the 1st Louisiana charged the union troops at a right angle upon the Crab Orchard road. Captain Mathews of company A, and the members of his company, were known to wear rattlesnake tails on their hats. Meanwhile Colonel Carter’s 1st Tennessee cavalry proceeded a few hundred yards and then charged pell-mell down the Crab Orchard road. Due to the terrain the 1st Louisiana was forced to fight dismounted. With the element of surprise gone the attack failed. For the first time in its history the 1st Louisiana was forced to give up ground it held.
During the next two hours the 1st Louisiana and 1st Tennessee retired fighting from various positions in an effort to delay the Union advance while Pegram took a new position on Sugar Hill approximately 2 and 1/2 miles south of Somerset. During the combat the 1st Tennessee lost its colors which had recently been presented to them by the daughter of General Marshall. The 1st Louisiana reported losses of 75 men. The 1st Tennessee reported losses of 37 men. After some half-hearted skirmishing, about 5:30 p.m., Pegram was allowed to withdraw under the cover of night. The Confederates crossed the Cumberland River at Stigall’s and Newell’s ferries with 537 of the 750 cattle that they had collected. General Pegram additionally claimed to have captured and paroled 178 Union soldiers. His losses were approximately 200 killed, wounded or missing. The Confederate prisoners were sent to Forts McHenry and Monroe. From there they were forwarded to City Point, Virginia, for exchange.
After the Battle of Dutton’s Hill, General Pegram ordered the arrest of Colonel Scott, court-martialing him for cursing a superior officer. Although found guilty, Colonel Scott received a light reprimand from General S. B. Buckner before being returned to command a brigade of cavalry.
Lt. Colonel Nixon filed six charges against General Pegram, which seem to have never been adjudicated by Confederate authorities.