Confederate Brig. Gen. John Gregg arrived in Raymond on May 11 with orders from Pemberton to contain the right flank of the Federal army as it advanced north and determine where it was heading. Thinking he faced a force only half the size of his, the combative Gregg decided to attack. To insure victory, Gregg devised an ambush in which one regiment would stop the Federal advance at Fourteenmile Creek while the two other regiments would cross over from the Gallatin Road and push the Federals against a bend in the deep creek bed of Fourteenmile Creek.
All in all, it was a good plan, except that Gregg's troops did not face an inferior force. Without sufficient cavalry to act as scouts, Gregg simply did not know how many Union Soldiers were marching up the road.
"The citizens (of Raymond) met us kindly and wonderingly. ... Early on the morning of the 12, the town was overrun with soldiers, having what we called a 'high old time.' In the midst of the fun, feasting, and coquetting the long roll sounded, and every man answered promptly. General Gregg moved through the town very quietly, where hundreds of people were eagerly watching events, little dreaming of the carnage to follow."
Private Sumner A. Cunningham, 41st Tennessee, CSA
"Captain Boone's company was thrown out as skirmishers, while we formed along the road in an excellent defensive position. While waiting here for the advance of the enemy, we learned that Captain Boone was killed while deploying his skirmishers. His death cast a momentary gloom over the regiment but the circumstance was soon forgotten in the excitement of the hour."
Pvt. W.J. Davidson, 41st Tennessee, CSA
"... we hadn't time to more than turn our heads when from out of the quiet woods on the other side of the brook, there came a great yell, of thousands of voices, followed by a crashing roar of musketry as one doesn't often hear unless he has been prepared for it."
Lt. Henry O. Dwight, 20th Ohio, USA