NHL 23

The Calder Trophy is the NHL's version of Rookie of the Year, so this achievement must be done your first year of Be A Pro. This is the fastest way I found to do the achievement:

Go to Offline and start a new Be A Pro Career as a Center (I chose Sniper, but it doesn't matter what you pick) and start in the NHL. Starting in other leagues means none of your games or stats will count. Pick whatever team you want, I picked the Washington Capitals but it doesn't matter. Now change these Game Settings:

-Game Style 1/4
-Period Length: your choice I like longer games so I can score a ton of points in a few games and then sim the rest out, but it's up to you for much you want to actually play
-Difficulty Rookie
-Injuries Off
-Be A Pro Settings Classic
-Be A Pro Simming Penalty Off (super important!)
-Auto Save On
-Playoff Series Length Single Knockout
-Icing Off
-Offsides Off
-Penalties 1/4

Then go into Gameplay Sliders and adjust every single slider in your favour: 100 for you, 0 for the CPU. Do notice this is the inverse for some of the settings like Dekes, so make sure to read the description to see which way to put the slider. With all settings done. start career. Sim through the Preseason, with Simming Penalty turned off you have no risk of getting sent down. Preseason stats don't count either.

It's very important to note here when you pay the games (play from the play tab and not the calendar), make sure your difficulty is set to Custom instead of Rookie. This lets you use your custom sliders. (Thanks GTAmissions1 for pointing this out!)

Once the regular season starts, you'll want to score 3 or 4 goals as quickly as possible. With the sliders adjusted you'll be unstoppable and once you get the hang of it can do this in under a minute. Once you have enough goals, pause the game and quit. This will sim the rest of the game and 99% of the time you'll win.

You want to repeat this for approximately 50 games or so, until you get the cutscene that you've clinched a playoff spot. There will be many, many other cutscenes along the way that are unskippable, get used to them. I always went with Team and Neutral answers when prompted because this helps raise your Legacy Meter towards the Golden Years achievement, but it doesn't really matter since you'll max that out soon enough.

Note: if you're planning on going for the Greatness achievement for breaking the all time record for points, feel free to play longer games or the rest of the season. The more you play, the more you will level up which will make your character more powerful when you are simming games.

Once you've clinched a playoff spot, create a new save file and sim the rest of the season to the playoffs. Your 50 games of goal scoring will be enough to win you the Calder Trophy, but you won't get that until after the Stanley Cup. When the playoffs start you only have to win four games thanks to the Single Knockout setting, and you can do the wins however you want. You can play the full games, sim the first two periods and intervene if you're losing, or just try simming them and reloading if you lose. If you are going to sim, make sure to create a new save file each time just in case.

After the fourth win you'll win the Stanley Cup Championship. A few cutscenes and screens will follow, one of which will award you the Calder Trophy and the achievement.