Mid-1800s Hockey is first played in Windsor, Nova Scotia, Montreal or Ontario... depending on who you believe.
1877 First known Official Rules for Ice Hockey are printed by the Montreal Gazette
1888 The Amateur Hockey Association of Canada forms, with four teams in Montreal, one in Ottawa and one in Quebec City.
1893           For $48.67, Lord Stanley purchases and donates a silver punch bowl for hockey competition. Montreal AAA wins the challenge.
1900 The goal net is introduced.
1910 The National Hockey Association (predecessor to the NHL) is formed.  
1911 Game format changes from two 30-minute halves to three 20-minute periods.
1912 The NHA drops the rover position and replaces a seven-man game with a six-man game
1917 The National Hockey League is organized on November 22. Montreal Canadiens, Montreal Wanderers, Ottowa Senators, Quebec Bulldogs and Toronto Arenas join the new league (Quebec does not begin until 1919 and the Wanderers withdraw after their arena burns down)
1919 The Montreal-Seattle Stanley Cup final is called off due to influenza epidemic.
1922 Foster Hewitt broadcasts the first NHL game on radio, between teams in Kitchener and Toronto.
1923 Boston becomes the first city in the United States of America to be awarded an NHL team, and defeat the Montreal Maroons 3-2 in the very first NHL game on American ice.
1927 NHL institutes rule that allows only team captains to address referees.
1928 Having no backup goaltender, 44-year-old Rangers coach Lester Patrick steps out of street clothes and into gear to replace injured goalie Lorne Chabot, beating the Montreal Maroons in game two of the Cup finals.
1934 The Great Depression forces the maximum team bulk payroll to drop from $70,000 to $62,500.
1936 The Detroit Red Wings and Montreal Maroons play the longest game in history, going to 6 overtimes and taking 5 hours and 51 minutes to complete.
1940 The Ross-Tyer puck is adopted as NHL's official game piece, but early in the season it is deemed too soft and replaced by the Spalding puck.

 

         

 

1942           Because of wartime restrictions on train scheduling, regular season overtime is discontinued.
1946 Gordie Howe joins the NHL at age 18, earning $2,600 in his rookie season.
1947 (Although one event for the benefit of Ace Bailey was held in 1933), The first of what would be the annual NHL All-Star Game is held in Toronto.
1948 Bill Durnan ends season as the last NHL goaltender to be team captain.
1949 Game ice is painted white.
1952 In the space of only 21 seconds, Chicago Blackhawk Bill Mosienko scores the fastest hat trick in history.
1955 Detroit clinches the Stanley Cup title in game 7, following the suspension of Canadiens star Maurice Richard giving way to the famous riot. Montreal went on to win 5 straight Stanley Cups in the years following.
1955 Referees wear striped shirts because their usual orange sweaters appear dark on black and white television, making it difficult to distinguish between them and away-team players.
1956 Montreal power play is so devastating, the NHL creates a new rule allowing player to come out of the penalty box after one man-advantage goal.
1957 Montreal's Jean Beliveau is the first hockey player to appear on the cover of "Sports Illustrated" magazine.
 

        

 

1959 After being stitched from a gash opened by a fast-moving puck, Montreal Canadiens goalie Jacques Plante stuns the hockey world by refusing to play unless he is allowed to wear the goalie mask he generally only used in practice.
1961 The Canadian National Exhibition, City of Toronto and NHL open the Hockey Hall of Fame on CNE grounds.
1967 The Original Six is doubled as the NHL undergoes its first major expansion.
1968 Montreal's Toe Blake retires after winning his 8th Stanley Cup, a record for NHL coaches.
1969 The NHL draft is expanded to include all amateur players of qualifying age throughout the world.
1970 Home teams are allowed to put their surnames on the backs of their sweaters; visitors need the home team's consent.
1970 By time of death, goalie Terry Sawchuck sets the unfortunate record of the most injuries, including: pierced eye, severed hand tendons, fractured foot, nine fractured ribs, dislocated arm, ruptured appendix, ruptured disc, punctured lung and over 400 facial stitches
1971 New England manufacturer draws criticism from religious groups for printing bumper stickers: "Jesus saves! And Esposito scores on the rebound!"
1972 Bobby Hull shocks the hockey world by signing a $2.75 million contract with the Winnipeg Jets in newly created World Hockey Association.
1976 Darryl Sittler sets an NHL record with 10 points in one game.
1977 Clarence Campbell retires after 32 years as NHL president and is succeeded by John Ziegler.
1977 All teams are required to put surnames of each player on the backs of sweaters.
1979 The World Hockey Assication dissolves; Winnipeg, Hartford, Edmonton and Quebec are brought into the NHL.
1980 Gordie Howe retires from professional hockey after playing 2,421 games and scoring a total of 2,589 points. He led the NHL in scoring 6 times during his career, and had been named to the All-Star team a record 21 times.
 
    
 
1981           Aluminum sticks are allowed for NHL play.
1983 Five-minute sudden-death overtime is instituted for regular season games.
1987 Philadelphia goalie Ron Hextall makes NHL history when he becomes the first goaltender to score a goal.
1989 Sergei Priakin is the first Soviet player permitted to sign with an NHL club.
1991 NHL institutes video replay to assist referees for review of goal/no-goal calls.
1992 The NHL turns to the National Baskteball Association for its new leader. Gary Bettman is named first commissioner.
1993 With the awarding of the 1993 Masterton, Mario Lemieux becomes the first player to win the Calder, Hart, Ross, Smythe and Masterton trophies.
1994 Wayne Gretzky scores his 802nd goal, surpassing Gordie Howe's all-time record.
1994 An NHL lockout lasts 101 days, forcing cancellation of 36 of each team's regularly scheduled games.
1997 Lord Stanley's Cup is taken on its first trip to Russia by Red Wings Viacheslav Fetisov, Igor Larionov and Vyacheslav Kozlov.
1999 The legendary "Great One" Wayne Gretzky retires from professional hockey.
2000 With continued expansion, the NHL reaches a total of 30 teams (6 in Canada, 24 in the US).
2004 Owners lock out the players, putting the season on hold, pending a new collective bargaining agreement.  The entire 2004-2005 season is later cancelled.
2005 When play resumes, the NHL makes a record number of rule changes, including instituting shoot-outs to end ties after the five-minute OT.