| 16th Century – Mi'kmaq communities playing a stick and ball game on the ice were observed by members of the British military. |
| 1895 – The Colored Hockey League of the Maritimes begins play. |
| 1902 – The Flett brothers, Magnus and Rod, and Tony Gingras, all of Metis heritage, become the first Indigenous players to win the Stanley Cup. |
| 1931 – The Preston Rivulettes women’s team dominates female hockey, winning 95% of all games over the next decade. |
| 1931 – Henry “Buddy” Maracle becomes the first “full-blooded” Indigenous player in NHL history. |
| 1932 – Ken Moore, of Cree heritage, wins a gold medal while representing Canada at the 1932 Olympic Games and is recognized as the first Indigenous athlete to win an Olympic gold medal. |
| 1948 – Larry Kwong, of Chinese heritage, breaks the NHL colour barrier. Canada had legislated the Chinese Exclusion Act of 1923, which wasn't repealed until 1947. |
| 1950 – Art Dorrington becomes first Black player to sign an NHL contract, but never plays in the League. |
| 1955 – Pierre Pilote joins the Chicago Black Hawks, becoming the first player of Inuit background to play in the NHL. Pilote did not disclose his heritage until after his retirement from hockey. |
| 1956 – Abby Hoffman is forced off her youth hockey team when it is revealed she is not a boy. Hoffman had cut her hair into a boy-ish style and played as 'Ab' until the discovery. |
| 1958 – Willie O’Ree becomes first Black player to appear in an NHL game. |
| 1962 – George Armstrong becomes the first captain of Indigenous descent to hoist the Stanley Cup. |
| 1984 – Goaltender Grant Fuhr becomes first Black player to win the Stanley Cup. |
| 1989 – Dirk Graham becomes NHL’s first Black captain. |
| 1990 – Robin Bawa becomes NHL’s first player of Indian descent. |
| 1992 – Manon Rheaume becomes the first woman to play an NHL game after tending goal in a pre-season match. |
| 1994 – Sledge hockey is added to the Winter Paralympics. |
| 1998 – Women’s hockey makes its Winter Olympic debut. |
| 2010 – Cammi Granato and Angela James become the first women inducted into the HHOF. |
| 2016 – Harrison Browne publicly comes out as a transgender man and thus becomes the first openly transgender athlete in professional North American hockey. |