On January 1, 1864, eighty members of Cole's Maryland Cavalry, led by Captain A. N. Hunter, entered the region colloquially known as "Mosby's Confederacy" around Upperville and Rectortown, Virginia. With Mosby off on a scout in Fairfax, Capt. William "Billy" Smith rounded up 32 Rangers and set off in pursuit of the Federals. The Rangers caught up with Hunter's force near Middleburg. Captain Hunter quickly deployed his men into battle line just as Smith ordered a charge. The Federal line soon crumbled when Hunter's horse was killed, tumbling the captain to the ground. The Union cavalry hastily retreated towards Middleburg, but not before losing 57 killed, wounded or captured, as well as 60 horses seized by the Rangers.