By November 1862, Northern Mississippi was securely in the hands of the Union army after key, yet costly, wins at Shiloh, Iuka, and Corinth.

After being defeated at the Battle of Corinth, Major General Earl Van Dorn's Confederate Army of West Tennessee was on the retreat.

The Confederate army kept falling back through Oxford and then Coffeeville, constantly skirmishing with pursuing Union cavalry, who were ahead of Grant's column.

Col Albert P. Thompson Unattached Outside of Coffeeville, the Confederate command decided to ambush the harassing enemy cavalry.

Around 2:30 pm, the Union Cavalry (led by Colonel Theophilus Lyle Dickey) approached Coffeeville within one mile.