The 2005–06 NHL season was the 89th season of operation of the National Hockey League (NHL). This season succeeded the 2004–05 season which had all of its scheduled games canceled due to a labor dispute with the National Hockey League Players' Association (NHLPA) over the Collective Bargaining Agreement (CBA) between the League and its players. The season featured the first time that all 30 of its member teams played games on the same day, which happened the first day of the season, October 5, 2005.

The Stanley Cup is the championship trophy awarded annually to the National Hockey League (NHL) playoff champion. It is the oldest existing trophy to be awarded to a professional sports franchise in North America, and the International Ice Hockey Federation (IIHF) considers it to be one of the "most important championships available to the sport". The trophy was commissioned in 1892 as the Dominion Hockey Challenge Cup and is named after Lord Stanley of Preston, the Governor General of Canada, who donated it as an award to Canada's top-ranking amateur ice hockey club. The entire Stanley family supported the sport, the sons and daughters all playing and promoting the game. The first Cup was awarded in 1893 to the Montreal Hockey Club, and winners from 1893 to 1914 were determined by challenge games and league play. Professional teams first became eligible to challenge for the Stanley Cup in 1906. In 1915, the National Hockey Association (NHA) and the Pacific Coast Hockey Association (PCHA), the two main professional ice hockey organizations, reached an agreement in which their respective champions would face each other annually for the Stanley Cup. It was established as the de facto championship trophy of the NHL in 1926 and then the de jure NHL championship prize in 1947.