
Before The Oil: Duke Keats, star of Edmonton’s Eskimos from the old WCHL and a future Hall-of-Famer, out for a country ramble during the 1921-22 season. In 1923, he missed a penalty shot in the Stanley Cup final, but he wasn’t the only one. (Image: Glenbow Archives, NC-6-8095)
Conor Sheary shot wide; when it was his turn, Jonathan Drouin tried for a backhand, but the puck wasn’t interested, and wandered wide.
The Montreal Canadiens exceeded the Pittsburgh Penguins last night in Toronto, 3-2 in overtime, with each team failing to score on a penalty shot. Sheary’s chance came in the third period, while Drouin failed to score in overtime as the NHL resumed its 2019-20 season with a flurry of Stanley Cup Qualifiers yesterday.
In the bold new world of the NHL’s emergency overhaul of its season, we’re not quite into the playoffs, yet — unless you’re talking about statistics and records-keeping. In that case, yes. As the league stipulates in its Return To Play manual, all these August games, round-robin and qualifying-round, “are considered part of the 2020 post-season,” and will go into the books as such.
Got it? Ready, then, for an historical note on the last time a playoff game featured a pair of penalty shots?
Good.
It was 97 years ago, since you’re wondering, on a Thursday at the end of March in 1923, in the first game of the Stanley Cup final.
That night, three penalty shots were awarded and duly taken. All three were failed efforts.
Vancouver was the scene, although (like last night) both of the teams involved were only visiting. In those years, up until 1926, the Stanley Cup final pitted the NHL champions against a western counterpart. In 1923, that meant the mighty Ottawa Senators were playing the Edmonton team from the old WCHL, who were called the Eskimos long before the CFL arrived in town.
The NHL didn’t adopt the penalty shot until 1934, but out west, where the canny Patrick brothers ran the PCHL, it had been in effect (for the WCHL, too) since 1921. The way it was then, when teams from rival leagues played for the Stanley Cup, they alternated rulebooks, game by game. The opening game of the ’23 final was played under western rules. Mickey Ion was the referee.
Ottawa prevailed that night, winning 2-1 in overtime thanks to a goal by Cy Denneny. Before that they’d failed to convert two penalty shots, while Edmonton missed one.
They did it differently, in those years. Instead of rushing in from centre-ice the way Sheary and Drouin did last night, a player 1923 saw the puck placed on one of three three-foot circles that were spread out across the ice in what we’d call the high slot, about 35 feet from the net. The shot would be taken from whichever circle was closest to where the infraction had taken place. Players had a choice: they could take the shot standing still, or they could make a skating start, building up speed as they approached the puck. They had to shoot it; carrying the puck to the net wasn’t allowed.
In 1923, Ottawa papers noted that the Senators’ disadvantage when it came to penalty shots, “something they were entirely unfamiliar with.”
In the first period, Ottawa defenceman Georges Boucher was on the rush when an Edmonton counterpart, Bob Trapp, tripped him. Ottawa sent in their leading scorer, Cy Denneny, to take the shot. Edmonton goaltender foiled him: he “dropped his stick,” the Ottawa Journal noted, “and caught the puck nicely.”
Later in the period, after Trapp took down Denneny, another Ottawa winger, Punch Broadbent, stepped up to take the penalty shot. “Although he directed it straight as a gun barrel,” Ottawa’s Citizen reported, “Winkler blocked it.”
In the third, up 1-0, Edmonton got its chance at a free shot when Ottawa defenceman King Clancy upended Eskimo winger Johnny Shepard. Edmonton sent in their top goalscorer to try his luck, the great Duke Keats, but his shot from the right-side spot didn’t trouble Ottawa goaltender Clint Benedict.
Back in Alberta, fans despairing after Denneny’s overtime winner put Ottawa ahead in the best-of-three final awoke next morning to find a column under Keats’ byline in the Edmonton Journal asking them not to worry. The Eskimos, he guaranteed, weren’t beaten yet — “not by a darn sight.”
It would be good to see something similar in the Pittsburgh Post-Gazette today from Conor Sheary, though it doesn’t seem to have materialized yet. Or maybe it should be another one for the Journal in Edmonton, this time under Connor McDavid’s name.
Of course, for Duke Keats in 1923, it didn’t work out so well. The Senators would wrap up the series the following day, that March, shutting out Edmonton 1-0 on Punch Broadbent’s goal to claim the Stanley Cup.

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