Keeling began his hockey career in his hometown, learning the game at Victoria Public School under the tutelage of principal Henry Kelso, for whom Owen Sound's Kelso Beach was named. Several Victoria students, including Keeling, eventually ended up playing for the city's junior club, the Owen Sound Greys. He was a key member of the Greys when they captured their first Memorial Cup as Canadian junior hockey champions in 1924, scoring an incredible 37 goals and 46 points in only 15 playoff games. He was 79 years old when he died suddenly at his Toronto home in 1984.