Huang Zhong initially served a military post under Liu Biao, governor of Jing Province. After Liu Biao's death in 208, Huang Zhong departed and served as a mercenary. He was working for Huan Xuan when Liu Bei invaded in 210. He tried to convince Huan Xuan to surrender, but he refused. During the night, Huang Zhong departed to meet with Liu Bei. He encountered Guan Yu, who challenged him. Awed by the old man's courage, Guan Yu escorted him back to the camp.
Huang Zhong's greatest victory was at Mount Dingjun, where he faced Xiahou Yuan. Each side had a solid defensive stance, so neither would advance. After several days, Huang Zhong fired a painted arrow into the camp, indicating that he wished a duel with Xiahou Yuan, a skilled archer. The archery duel lasted two days before Xiahou Yuan was struck and killed. The rival army, now in disarray, was easily set to rout. However, the effort exhausted Huang Zhong, who returned to camp for medical treatment.
As a result of the victory, Huang Zhong was declared one of the Five Tiger Generals. A month later, he suffered a heart attack and died.