Over a period of twenty years, Rogan participated in many skirmishes and expeditions mounted against the Native Americans who controlled what is now Middle Tennessee. While it may be argued that the enmity between Ireland and England provided Rogan with circumstances which promoted, even invited and encouraged armed conflict, it is also apparent that he readily transferred his bravery, hostility, and considerable aptitude for nontraditional warfare towards the Indians. While it is a reality that the native tribes against whom he fought were defenders, just as he was in Ireland, of their land, livelihood, and culture from invading forces, it is almost a certainty that Rogan and other European settlers never viewed the conflict in this light.
Hugh Rogan was generally admired and respected, even considered a legend by some who knew him. As an example, in 1787 he was one of several men, under the command of James Robertson, who traveled south into Alabama to confront a band of Creek and Cherokee renegades in the well-documented Cold Water Expedition. After destroying the camp, Rogan was one of several who were severely injured during a reprisal by Indians who escaped. Chronicler, W. W. Clayton, described Rogan as a man of superlative courage and strength of will who, though shot through one lung, still marched back to Fort Nashborough carrying his gun and gear.
This part of family history was remembered by Clarissa Rogan, Hugh's only granddaughter. In 1858 she wrote in her journal that "Grandpa Rogan "was" shot thru the body at the mouth of the Duck River in June 1787."
Clayton also relates another tale of Rogan's courage. Indians attacked Bledsoe's Lick wounding several men including Colonel Anthony Bledsoe. Bledsoe, who knew he was dying, asked for a fire to be lit so he could dictate and sign his will. Otherwise, his daughters could not inherit his considerable holdings. No live embers, however, could be found in the stockade. Rogan was the only one willing to face the night and almost certain attack. He slipped out to the nearby cabin of a woman who was superstitiously feared and avoided by Indians and returned with coals for a fire. The will was written, signed, and Bledsoe died a few hours later. Those who witnessed the event never forgot Rogan's courage.