Hockey League Simulator was the first true "General Manager" hockey simulation ever made. It gave you complete control over the entire league and allowed you to choose as many human or computer owners/GM's as you wanted not to mention you could create leagues of almost any size and configuration.
While it was very rudimentary it did allow for player creation, salaries (though no salary cap) and team creation. Also you trade with the computer despite the fact that the trade logic was occasionally shaky (I recall once trading Wayne Gretzky for Doug Wickenheiser).
But without any doubt what made Hockey League Simulator special was the fact you could export your team’s games then import them into Wayne Gretzky's Hockey or Wayne Gretzky's hockey 2 and play the game then export the final game stats back into Hockey League Simulator.
I recall when I was young and had my computer in my parents’ undeveloped basement having my league setup written on the walls along with the realignments I did and also would go through and completely edit every player in the NHL making stats based on what they had done in the previous season. So needless to say I was very excited when I saw this game available to download.
It had a few flaws
but at the end of the day this is still one of the best league tools ever made. I highly recommend trying it out for yourself. An easy 9.5/10