Keeling became an Ottawa Rough Rider from 1973 to 1975.

He played professional football for the Ottawa Rough Riders in 1934.

He finished his football days with the Ottawa Rough Riders in 1955.

He also served as the director of football operations for the Ottawa Rough Riders from 1995-1996.

In 1991 he was the secondary coach of the Ottawa Rough Riders.

He played football for the Ottawa Rough Riders between 1912 and 1923.

He finished his career the Ottawa Rough Riders, having score 510 points.

He would finish his career in 1984, after being traded to the Ottawa Rough Riders.

He was head coach of the Ottawa Rough Riders from 1989-91.

He joined the Ottawa Rough Riders for one season, 1981, and was again an all star.