Cunningham was born at Volant, Pennsylvania in July 1872. His father, Valentine Cunningham, was a native of Grove City, Pennsylvania. Cunningham was a 5-foot, 9-inch, 180-pound native of Grove City, Pennsylvania who played center for the University of Michigan Wolverines from 1897-1899. Chosen as an All-American in 1898, he was the first University of Michigan football player to be so honored. The 1898 Wolverines went 10-0 and won the Western Conference (now known as the Big Ten Conference) championship. The first great Michigan football team, the 1898 group outscored its opponents 205 to 26. They shut out Michigan Agricultural College (39-0) and Notre Dame (23-0) before traveling to Chicago for a final game against Amos Alonzo Stagg's University of Chicago team on November 24, 1898. Led b