The Windsor Hotel in Montreal was first used by Hockeyists during the mid 1880s, when the the famous Montreal Winter Carnivals were held, with Carnival events in the square just across the street from the hotel. The Victoria Skating Rink was just a block away, where Winter Carnival Hockey games were played, and the 1st Stanley Cup playoff games in 1894.

On December 10, 1898 representatives of the Quebec Bulldogs, Montreal Victorias, Ottawa Hockey Club and Montreal Hockey Club met at the Windsor Hotel. On December 14, the group met again and organized the Canadian Amateur Hockey League / CAHL, also adding the Montreal Shamrocks.

The CAHL league would stay with five teams until the 1904 season.

On November 22, 1917 Montreal Wanderers owner Samuel Edward Lichtenhein, Montreal Canadiens owner George Kennedy, Ottawa Senators owner Tommy Gorman and Quebec Hockey Club manager Mike J. Quinn of the National Hockey Association / NHA met in one of the Windsor Hotel's restaurants and agreed to form the National Hockey League / NHL.

The NHL officially began on November 26, 1917 when the documentation was signed by the teams owners at the Windsor Hotel, naming Frank Calder as the 1st NHL president.

The first board of directors of the National Hockey League / NHL were also elected.
- Samuel Edward Lichtenhein / S.E. Lichtenhein / Montreal Wanderers
- Martin Harold Rosenthal / M.H. Rosenthal / Ottawa Senators
- George Washington Kendall / G.W. Kendall / Montreal Canadiens

Michael James Quinn / M. J. Quinn was elected Honorary President with voting power on matters pertaining to the general welfare of the league.

The Quebec Bulldogs, while a member, did not operate in the NHL for the first two years and its players were divided up among the other clubs. Instead William Northey, owner of the Toronto Arena Gardens wanted a new Toronto franchise and his club would eventually be called the Toronto Arenas / Blue Shirts.

The stately building was the ideal setting for the meetings that would bring the NHL to life, constructed to serve the rail passengers of nearby Windsor Station and serving as the residence of the Canadian Pacific and Grand Trunk railways. From the NHL's founding in 1917 well into the 1960s, the Canadiens and visiting NHL teams arrived in Montreal and departed the city from the majestic train station.

Other Hockey leagues held meetings at The Windsor Hotel also - Montreal Commercial Hockey League, Montreal CPR Hockey League, Montreal Bank Hockey League, Montreal Bell Telephone Hockey League and the Montreal Hotels Hockey League.

The Windsor Hotel first opened on January 28, 1878, then had a major fire in 1906, which simply prompted significant renovations and the addition of a new wing, known as the Windsor Annex, to the north of the original building. The number of rooms more than doubled, going from 368 to 750, and the hotel now occupied an entire city block. The Windsor annex contained the famous "Peacock Alley" (named after the peacock designs in its stained glass windows), and two additional ballrooms.

In 1957, another fire destroyed a third of the hotel. This time the damage was extensive, and the original hotel structure had to be demolished.

The North Annex was all that remained of the Windsor Hotel, but it did contain 200 guest rooms, two ballrooms and Peacock Alley. The Windsor Hotel continued to operate out of the North Annex for almost another 25 years, but competition from newer hotels led to the Windsor's slow decline, and it finally closed it's doors in 1981.

In 1987, the Windsor Hotel reopened as an office building called "Le Windsor". Peacock Alley and a number of marble staircases have been preserved, and the two ballrooms are still used for banquets, wedding receptions and conferences.

NOTE
There is a plaque in Le Windsor that was unveiled in 2017 by the Historic Sites and Monuments Board of Canada in conjunction with the National Hockey League, the plaque commemorates the founding of the league during a meeting at the hotel 100 years earlier.