Though he didn't begin playing competitive football until he was a student at Queen's University, Ben Simpson immediately stood out above the rest. After leading the Queen's intermediate team to a decisive victory over the University's senior team, coaches took notice of the young freshman's impressive kicking skills and invited him to play for the senior team. Simpson played for Queen's until his graduation in 1903, leading the school to the intercollegiate union championship in 1900. When he moved to Hamilton to attend the College of Education in 1904, the Hamilton Tigers were quick to add him to their roster. In his six years as a star halfback and kicker with the Tigers, Simpson helped them capture the provincial title in 1904, 1905, and 1906, as well as the Interprovincial Rugby Football Union title in 1908. In 1910, Simpson captained them to their very first Grey Cup appearance. Simpson retired from the field shortly thereafter but officiated in the interprovincial and intercollegiate leagues for the next six years. An educator by profession, Simpson taught, coached, and served as principal at schools around the Hamilton area until his retirement in 1947. For his outstanding performance on the football field, Simpson was inducted in to the Canadian Football Hall of Fame in 1963.