The Stanley Cup is the only Big Four championship that predates its league. Lord Stanley commissioned the iconic trophy to honor the best Canadian hockey team in 1892, 25 years before the NHL was founded. For most of its pre-NHL history, trustees arranged competitions for the Cup like title fights in boxing; whichever team won the Cup received challenges from teams in rival leagues. 

It wasn’t always that easy, though. Strange rules, debates over Lord Stanley’s intentions, and feuds among trustees, leagues, and teams made early competitions messy. Here are some memorable moments in the history of “hockey’s holy grail.” 

1. The First Upset (1892-93) 

Today’s players eagerly hoist and kiss the Cup after winning it. Not so in the trophy’s inauspicious inaugural year. The first champs were the Montreal Hockey Club, a group “connected” with the Montreal Amateur Athletic Association. Because the team wasn’t fully affiliated, the MHC received less funding and fewer benefits than proper affiliates, yet the association took full credit for any success. When the MHC won the Cup, the club’s players were angered to find “Montreal AAA” engraved on the chalice. It wasn’t until just before they won the trophy again the following year that the club begrudgingly accepted the trophy. 

2. The Tournament that Never Happened (1894-95) 

Any hockey fan knows that teams have to play for the Cup, but that wasn’t always the case. When the Montreal Victorias finished atop their league’s standings, they expected to receive the Cup automatically. However, a title match had already been scheduled between the previous year’s champs (MHC) and Queen’s University. The Vics offered to play in MHC’s stead, but the trustees insisted that the match proceed as scheduled. When MHC beat Queen’s, the trustees delivered the Cup to the Vics because they’d already beaten MHC in the standings. Thus, the Victorias won the Cup without officially playing for it. 

3. Emerging Victorias (1895-96) 

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Confusion reached new heights in 1896, when two Cup matches were scheduled between the Winnipeg Victorias and the Montreal Victorias. In those days, nothing epitomized fierce competitiveness like showing fealty to the British monarchy. In the first meeting, the W-Vics took the Cup from the M-Vics. In the second, the M-Vics reclaimed the trophy from the W-Vics. Of course, the real losers were sportswriters who were tasked with sorting through this moniker mess. 

4. The Concession Cup (1896-97) 

The proliferation of amateur leagues became problematic for the trustees, who struggled to ensure that new teams were worthy of challenging for the Cup. One iffy challenger was the Ottawa Capitals, who faced the Montreal Victorias in a best-of-three series. After Montreal trounced Ottawa 15-2 in the first game, the humiliated Capitals conceded the series. 

5. Rounding Up (1901-02) 

During one heated Cup match, the puck broke in two. Undeterred, a Toronto player corralled one half and fired it past Winnipeg’s goalie to score the most divisive goal in Stanley Cup history. When a similar situation happened in a 1900 game, referee Fred Waghorne disallowed the goal, arguing that players could only score with whole pucks. Waghorne’s decision is the one most often used, and led to the development of one piece pucks.  

6. The Curfew Mulligan (1902-03) 

Today’s fans know that playoff games are like the seventh rule of Fight Club: They go on as long as they have to. That wasn’t the case in 1903, when an overtime game was abruptly halted to comply with a mandatory curfew in Montreal. The game was replayed in full two days later, rendering both teams’ previous efforts moot.    

7. Trash-Talk Debuts (1903-04) 

The Ottawa Silver Seven became mired in controversy when commentators alleged that the reigning champs won using bone-crunching gamesmanship rather than skill. During a showdown between Toronto and Ottawa, the Toronto Star wrote, “Marlboros Beaten by Ottawa, But Not at Hockey.” When Ottawa played cleanly in the second game and clinched the series, the Ottawa Citizen mockingly referred to the Toronto media as the “squealers from Squealville.” 

8. Unbreakable Records (1904-05) 

Road-weary NHL players should find some perspective on their own travel issues by remembering the Dawson City Nuggets, who traveled 4000 miles from December 18 to January 11 to challenge Ottawa. They arrived in Canada’s capital just two days before the best-of-three tournament began. Losing the first game 9-2 was the high point for the club from Yukon. They lost the second 23-2, the highest goal total and worst goal differential in Stanley Cup history. Ottawa’s Frank McGee set another record in the rout by scoring 14 goals, the highest tally ever achieved by one player in a Stanley Cup game.  

9. Snatching Defeat from the Jaws of Victory (1905-06) 

Ottawa faced Montreal in a two-game Cup challenge in which the team scoring the most cumulative goals won. Montreal won the first game 9-1. In the second, Ottawa led 9-1, tying the series at 10-10. However, Montreal rallied to score twice more, losing the game 9-3 but winning the series 12-10. Imagine how today’s riotous fans would react to seeing a team walk away with the Cup after getting throttled in a game!   

10. The Underdog Capital of Canada (1906-07)

With just 6000 residents, Kenora, Ontario became the smallest town to win the Cup when the hometown Thistles beat the Montreal Wanderers. Unfortunately, the Thistles also set the record for the shortest reign. Sixty-four days after beating Montreal, Kenora lost a rematch and handed the Cup back to the Wanderers.

11. Ticket Scalping Turns Pro (1907-08) 

Hockey became more profitable as fans took greater interest in rivalries, and the biggest rivals of the era were the Ottawa Silver Seven and the Montreal Wanderers. When each team’s hopes of competing for the Cup were on the line in 1908, scalpers resold $1 tickets for $20 each. Despite the 1900 percent markup, there was no shortage of buyers as 7000 fans packed the Montreal Arena while thousands outside broke windows and doors trying to get in. 

12. The Yanks Are Coming (1915-17) 

As interest in hockey grew, Americans clamored to compete for the Cup. The trustees initially refused, arguing that Lord Stanley had intended his silverware to be fought over by Canadians only. The trustees maintained that position until 1915, when they made an abrupt about-face by declaring the trophy open to competitors worldwide. (Sorry, extraterrestrials.)  

In 1916, the first international match began as the Portland Rosebuds faced the Montreal Canadiens. The following year, the Seattle Metropolitans became the first American team to carry the Cup across the border. Canada’s sport had officially developed from a regional pastime to an international enterprise.