October 25, 1863 – in Pine Bluff, Arkansas – At 8:00 A.M., October 25, Col. Powell Clayton sent a company of cavalry toward Princeton which ran into Brig. Gen. John S. Marmaduke’s men advancing, out on a raid against the important Union garrison. After some fire, the Confederates, under a flag of truce, came forward demanding surrender. Lt. M.F. Clark answered that there would be no surrender. Clayton slowly retreated back into Pine Bluff. In the meantime, about 300 African-American soldiers rolled cotton bales out of the warehouses for barricades to protect court square. After failing to take the square by force, the Confederates attempted to burn out the Union forces but to no avail. The Confederate forces retired, leaving Pine Bluff to the Federals. The federals suffered 11 killed and 27 wounded. The confederates suffered 53 killed & 164 wounded.