From 1933-34 here is a rare hockey game called Apple Leaf Hockey:
From 1937 here's All Star Hockey. It is simply a board (rink) is marked off in squares and the pawns used to represent players move from square to square depending on a die roll.
In 1941 Milton Bradley dreamed up Ice Hockey: The game comes with 1 wooden disc and two wire hockey "crooks". You play the game by first placing the disc on the center spot on the boards and then each player takes a wire crook and then trying to draw or knock the wooden disc (puck) through the goal to the players right. The opponent plays at the same time, each player trying to get the puck into their goal. The game is started by one player tapping 3 times and then calling 'GO!" The game is played to a predetermined number of gaols. The player reaching that pre-determined number wins.
Here's a Lester Patrick endorsed hockey board game from the 1940s. This game came in two formats one that used a die but earlier versions came with a spinner for randomization. The players are printed on the board and movement is the puck from square to square. There are printed squares on the board that if you take the puck to will can cause penalties to the opposing player in various ways including giving you a penalty shot on goal from a designated spot on the board that is also resolved with a die roll.
From the 1950s, here's The National Hockey League Game
Harley Productions came out with He Scores! in 1955. This game combines all the thrills of real hockey and is played on a board representing the ice surface. Players are shown in both Red and Blue. The game has two dice and a puck which is moved through squares in the direction and by the distance of what was rolled on the dice. Game appears to feature pictures of both the Montreal Canadians and the Toronto Maple Leafs.
In 1959 Negameco came out with this stat-driven game for simulating professional hockey matches.
From the 1960s, here's Pass And Score, fun for the whole family:
From 1968, here's Blue Line Hockey
All Pro Hockey came out in 1969.
Here's a game called Power Play from 1970. I'm not sure if there are other teams than just Vancouver or not. I want to say I saw a Minnesota version once upon a time, too.
Also in 1970 Research Games released Rod Gilbert's Violent World of Pro Hockey. It was actually part of a 5 game series of Rocky Graziano (Boxing), Vince Lombardi (Football), Gil Hodges (Baseball), Rod Gilbert (Hockey), and Oscar Robertson (Basketball).
From 1974 here's Face Off, the hilarious hockey management game:
Then there is the legendary Strat-O-Matic Hockey card and dice game. This game realistically simulates managing your lines, assigning players, how aggressive or defensive to be, and for the statisticians in the crowd, you can even keep score right down to the number of shots per period, time of goals, assists, etc.
This following game is so old, you needed something called a VCR. I had this game when I was a kid. Players move around the board drawing cards and doing what is says on the space. If you land on "VIDEO ATTACK" you go to the VCR to see what happens. It shows a great play from a game in the past. Either a goal or a save. If you see a goal you score a point.
I also had this trivia board game called Hockey Challenge. No one played with me because I knew all the answers. Then the questions got out of date as many of the answers changed with new records set etc.
I'm not sure how old this particular card game is, but I bet it is relatively contemporary.
If you know any more details about these or any other hockey board games, feel free to share your memories in the comments section.