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 37 goals and 46 points in 15 playoff games.
[1][2] Keeling's pro career began in 1926–27 with the London Panthers of the Canadian Professional Hockey League, although he was quickly elevated to the NHL's Toronto St. Patricks, with whom he had signed as a free agent on September 7, 1926.
Despite playing in only 30 of Toronto's 44 games, Keeling finished fourth in team scoring with 11 goals and 13 points, right behind fellow Owen Sound native Hap Day.
Toronto's Maple Leaf Gardens was the site of Game 4 of the 1933 Cup Finals, and the Rangers held a 2–1 lead in the best-of-five series.
Bill was Bill Cook, oldest active player on the Rangers, leading scorer of the National League ... (Cook) took the puck without breaking his stride, feinted to bring tall Lorne Chabot away from the Toronto net, then flipped the puck over Chabot's shoulder for the goal that ended the game 1 to 0, the series 3 to 1.
He left the NHL after the 1937–38 season and played one year with the Philadelphia Ramblers, a Rangers farm team in the International-American Hockey League.