Sent out west to the frontier, Woodall became an experienced Native American fighter and eventually reached the rank of sergeant.

On the morning of September 12, 1874, Woodall led a 6-man courier detail including cavalry troopers Pvt.

On their way to the wagon train, Woodall and his men were suddenly ambushed and encircled by a force of 125 Native Americans at the Washita River.

Making their way to a nearby buffalo wallow, they continued fighting the Native Americans throughout the day and managed to hold the hostiles off despite being outnumbered 25-to-1.

They were eventually found by members of the 8th U.S. Cavalry, then rescued by Colonel Miles' troops and brought to Fort Supply to recover from their wounds.