Cutshaw served under General Jubal Early during the Valley Campaigns of 1864, but missed the Third Battle of Winchester as he was raiding behind Federal lines in newly-established West Virginia. As Confederate defeat seemed inevitable in 1865, he received a severe leg wound during the Battle of Sailor's Creek, three days before General Robert E. Lee's surrender at Appomattox. Doctors saved Cutshaw's life, but amputated his leg.