[4] He won the Stanley Cup with the Millionaires in 1915 as they defeated the Ottawa Senators of the National Hockey League for the Canadian championship.

[4] He then fought to regain his amateur status so that he could take on the role of player-coach with the Edmonton Eskimos of Alberta's Big-4 League.

[9] Following the collapse of the WCHL in 1926, Stanley purchased the Eskimos and brought them into the newly formed Prairie Hockey League.

[11] He purchased an ownership stake in the franchise, and signed on as a defenceman and coach for the American Hockey Association team.

[4] Stanley returned to the AHA, playing his final season of hockey with the Minneapolis Millers before retiring in 1929.

[16] He was a member of the hockey committee of the Edmonton Exhibition Association when the Flyers won the Allan Cup national senior championship in 1948.

[13] Stanley also designed one of the sport's first hockey helmets, presented to the NHL's board of governors without interest after Chicago's Dick Irvin suffered a fractured skull during a game.