By the Letters: “W” for Wins (and Winners)
In a previous Professors’ Press Box article, letter “L” was explored; specifically, how all-time losses in NHL history can serve as a strange badge of longevity. Today, the page is turned to a more celebrated column; letter “W” for “Wins.” Scan the list of franchises with the ”Most Wins All-Time” and you'll see a familiar pattern. The "Original Six" dominate the peak. Just as they led the way in losses, these six franchises—the NHL's foundation from 1942 to 1967—rightfully claim the top spots for all-time wins (as of March 24, 2026).
1. Montreal Canadiens (3,634 Wins): The Montreal Canadiens sit alone at the summit. For the Canadiens, winning isn't just a goal; it's a cultural expectation. This massive win total provided the bedrock for their 24 Stanley Cup championships, the most in league history.
Cool Fact: The Montreal Canadiens became the first team in NHL history to reach 3,000 wins (5–2 win; December 29, 2008).
2. Boston Bruins (3,476 Wins): Since joining in 1924 as the league’s first American expansion team, the Boston Bruins’ win column is bolstered by legends like Gerry Cheevers, Bobby Orr, Phil Esposito, Ray Bourque, Cam Neely, Brad Patrice Bergeron, Brad Marchand, along with a recent record-shattering 65-win campaign (2022-23).
Cool Fact: The Boston Bruins won the first ever NHL game played in the USA on December 1, 1924 (Montreal Maroons at Boston Arena).
3. Toronto Maple Leafs (3,231 Wins): Aside from the well-documented Stanley Cup championship drought, the pure volume of “wins” the Toronto Maple Leafs organization has posted since 1917 cannot be argued. From the dynasty years of the 1940s and 1960s to the high-octane Auston Matthews era of today, the Maple Leafs organization has piled up regular-season wins throughout their history, representing one of the deepest legacies in professional sports.
Cool Fact: Punch Imlach coached the most regular season games of any Maple Leafs' head coach (770 games)—earning the most all-time points (865 points); followed by Pat Quinn (574 games as the Maple Leafs’ head coach; 678 points).
W: Winning Ways in NHL History
The “Original Six” sweep is completed by the Detroit Red Wings (3,174), New York Rangers (3,104), and Chicago Blackhawks (2,940). In the end, letter “W” represents the ”Most Wins All-Time”; milestones of hockey history, proving that the greatest winners are teams that have stood the test of time.