In 1914, a year in which he was captain, he led the Sewanee eleven to the first defeat of rival 1914 [Vanderbilt Commodores football team|Vanderbilt] since 1909. Tolley was awarded a gold football charm to commemorate the 14 to 13 victory. One account reads "For brilliance and beauty of execution, has had few equals, if any, in the South, and the Tiger leader retires from the game as the premier quarterback in the S.I.A.A., beyond a doubt." His performance included a 75-yard punt return for a touchdown.