[1] He joined that city's junior team, the Owen Sound Greys, and led them to the 1924 Memorial Cup as Canadian champions.

[2] After the Greys lost the 1925 OHA final to Toronto Aura Lee, Weiland began a three-year stint with the Minneapolis Millers of the old American Hockey Association.

That led to the start of his NHL career with Boston, where he celebrated his rookie campaign in 1928–29 with a Stanley Cup victory over the New York Rangers.

Weiland flourished under those conditions, shattering the NHL's single-season points record of 51 which had been set two years earlier by Montreal Canadiens legend Howie Morenz.

Weiland scored four goals in Boston's 7–0 victory over the Pittsburgh Pirates on February 25, 1930, becoming the third Bruin to achieve the feat.

But he ended his NHL playing career as he had begun it; the Bruins defeated the Toronto Maple Leafs and earned their second Stanley Cup.

Weiland coached seven All-Americans, including three-time first-team selection Joe Cavanagh '71 and two-time pick David Johnston '63.